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Journal articles on the topic 'Amide bonds'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Wilbrand, Sabine, Christian Neis, and Kaspar Hegetschweiler. "(S)-2,2′-Dihydroxy-N,N′-(6-hydroxyhexane-1,5-diyl)dibenzamide." Acta Crystallographica Section E Structure Reports Online 69, no. 2 (2013): o223. http://dx.doi.org/10.1107/s1600536813000354.

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In the title compound, C20H24N2O5, the dihedral angle between the two roughly planar salicylamide fragments [r.m.s. deviations = 0.043 (2) and 0.149 (2) Å] is 25.50 (5)°. The molecular conformation is stabilized by intramolecular O—H...O hydrogen bonds involving phenol –OH groups and amide O atoms. Intermolecular hydroxymethyl–amide O—H...O and amine–hydroxymethyl N—H...O hydrogen bonds form infinite chains along thebaxis. These chains are further interlinked by amine–amide N—H...O and phenol–phenol O—H...O interactions, thus giving layers parallel to (001).

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2

Mahesh, Sriram, Kuei-Chien Tang, and Monika Raj. "Amide Bond Activation of Biological Molecules." Molecules 23, no. 10 (2018): 2615. http://dx.doi.org/10.3390/molecules23102615.

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Amide bonds are the most prevalent structures found in organic molecules and various biomolecules such as peptides, proteins, DNA, and RNA. The unique feature of amide bonds is their ability to form resonating structures, thus, they are highly stable and adopt particular three-dimensional structures, which, in turn, are responsible for their functions. The main focus of this review article is to report the methodologies for the activation of the unactivated amide bonds present in biomolecules, which includes the enzymatic approach, metal complexes, and non-metal based methods. This article als

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3

Gautier, Yohan, Thierry Maris, and W. G. Skene. "Crystal structure of diethyl 2-amino-5-{4-[bis(4-methylphenyl)amino]benzamido}thiophene-3,4-dicarboxylate." Acta Crystallographica Section E Crystallographic Communications 75, no. 5 (2019): 589–92. http://dx.doi.org/10.1107/s2056989019003864.

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In the title compound, C31H31N3O5S, the regioselective substitution of the thiophene is confirmed with the amine and the amide at the 2- and 5-positions, respectively. In the molecule, the thiophene ring is twisted by 12.82 (3)° with respect to the aromatic ring of the benzamido group. Intramolecular N—H...O hydrogen bonds are present involving the N atoms of the primary amine and the amide groups, forming S(6) ring motifs. In the crystal, centrosymmetrically related molecules are linked by pairs of N—H...O hydrogen bonds involving the amide carbonyl O atoms and the primary amine N atoms to fo

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4

Wang, Zhe, Akira Matsumoto, and Keiji Maruoka. "Efficient cleavage of tertiary amide bonds via radical–polar crossover using a copper(ii) bromide/Selectfluor hybrid system." Chemical Science 11, no. 45 (2020): 12323–28. http://dx.doi.org/10.1039/d0sc05137c.

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5

Ntsala, Lerato P., and Andreas Lemmerer. "6-Aminonicotinamide." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (2012): o2449. http://dx.doi.org/10.1107/s1600536812031224.

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In the title compound, C6H7N3O, the amide group is rotated such that the carbonyl O atom issynto the pyridine N atom, with an O—C—C—C torsion angle of −23.55 (18)°. The crystal packing involves four hydrogen bonds of the types N—H...N and N—H...O. Two separate centrosymmetric rings are formed using N—H...N and N—H...O hydrogen bonds that result in a ribbon of 6-aminonicotinamide molecules, joined by the amide and amine functional groups. The remaining two hydrogen bonds are used to generate a three-dimensional packing arrangement.

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6

Zhao, Fei, Pinyi Li, Xiaoyan Liu, Xiuwen Jia, Jiang Wang, and Hong Liu. "Recent Advances in the Addition of Amide/Sulfonamide Bonds to Alkynes." Molecules 24, no. 1 (2019): 164. http://dx.doi.org/10.3390/molecules24010164.

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The addition of amide/sulfonamide bonds to alkynes is not only one of the most important strategies for the direct functionalization of carbon–carbon triple bonds, but also a powerful tool for the downstream transformations of amides/sulfonamides. The present review provides a comprehensive summary of amide/sulfonamide bond addition to alkynes, including direct and metal-free aminoacylation, based-promoted aminoacylation, transition-metal-catalyzed aminoacylation, organocatalytic aminoacylation and transition-metal-catalyzed aminosulfonylation of alkynes up to December 2018. The reaction condi

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7

Liu, Yongliang, Rae-Kwang Cho, Kaori Sakurai, Tsuyoshi Miura, and Yukihiro Ozaki. "Studies on Spectra/Structure Correlations in Near-Infrared Spectra of Proteins and Polypeptides. Part I: A Marker Band for Hydrogen Bonds." Applied Spectroscopy 48, no. 10 (1994): 1249–54. http://dx.doi.org/10.1366/0003702944027408.

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FT-NIR spectra have been measured for various polypeptides and proteins with different secondary structures to find an NIR marker band for the structure of the proteins and polypeptides. Their FT-IR spectra have also been obtained to assist in the interpretation of the FT-NIR spectra. Comparison between the FT-NIR and FT-IR spectra shows that there is a clear correlation between the frequency of an NIR band near 4855 cm−1, assignable to a combination of amide A and amide II, and that of an IR band near 3300 cm−1 due to amide A for the polypeptides investigated. Therefore, the NIR band (hereaft

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8

Tan, Ming Yueh, Karen A. Crouse, Thahira B. S. A. Ravoof, Mukesh M. Jotani, and Edward R. T. Tiekink. "1-{(E)-[(2E)-3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-ylidene]amino}-3-phenylurea: crystal structure and Hirshfeld surface analysis." Acta Crystallographica Section E Crystallographic Communications 73, no. 11 (2017): 1607–11. http://dx.doi.org/10.1107/s2056989017014128.

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The title compound, C23H21N3O2, is constructed about an almost planar disubstituted aminourea residue (r.m.s. deviation = 0.0201 Å), which features an intramolecular amine-N—H...N(imine) hydrogen bond. In the `all-trans' chain connecting this to the terminal methoxybenzene residue, the conformation about each of the imine and ethylene double bonds isE. In the crystal, amide-N—H...O(carbonyl) hydrogen bonds connect centrosymmetrically related molecules into dimeric aggregates, which also incorporate ethylene-C—H...O(amide) interactions. The dimers are linked by amine–phenyl-C—H...π(imine–phenyl

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9

Scheidt, Karl. "Amide bonds made in reverse." Nature 465, no. 7301 (2010): 1020–22. http://dx.doi.org/10.1038/4651020a.

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10

Long, Augustin, Olivier Perraud, Erwann Jeanneau, Christophe Aronica, Jean-Pierre Dutasta, and Alexandre Martinez. "A hemicryptophane with a triple-stranded helical structure." Beilstein Journal of Organic Chemistry 14 (July 24, 2018): 1885–89. http://dx.doi.org/10.3762/bjoc.14.162.

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A hemicryptophane cage bearing amine and amide functions in its three linkers was synthesized in five steps. The X-ray molecular structure of the cage shows a triple-stranded helical arrangement of the linkers stabilized by intramolecular hydrogen bonds between amide and amine groups. The chirality of the cyclotriveratrylene unit controls the propeller arrangement of the three aromatic rings in the opposite part of the cage. 1H NMR studies suggest that this structure is retained in solution.

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11

Miyabe, Hideto. "Transition-Metal-Free Activation of Amide Bond by Arynes." Molecules 23, no. 9 (2018): 2145. http://dx.doi.org/10.3390/molecules23092145.

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Highly reactive arynes activate the N–C and C=O bonds of amide groups under transition metal-free conditions. This review highlights the insertion of arynes into the N–C and C=O bonds of the amide group. The insertion of arynes into the N–C bond gives the unstable four-membered ring intermediates, which are easily converted into ortho-disubstituted arenes. On the other hand, the selective insertion of arynes into the C=O bond is observed when the sterically less-hindered formamides are employed to give a reactive transient intermediate. Therefore, the trapping reactions of transient intermedia

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12

Mitchell, John B. O., and Sarah L. Price. "On the relative strengths of amide…amide and amide…water hydrogen bonds." Chemical Physics Letters 180, no. 6 (1991): 517–23. http://dx.doi.org/10.1016/0009-2614(91)85003-f.

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13

Rychlewska, Urszula, Wioletta Bendzinska-Berus, Agnieszka Janiak, and Beata Warzajtis. "Mono- & ditrityl ethers, amines & amides – a family of multifaceted materials." Acta Crystallographica Section A Foundations and Advances 70, a1 (2014): C670. http://dx.doi.org/10.1107/s2053273314093292.

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In the course of our recent study on the possible transfer of chirality from the stereogenic center(s) to the inherently helical triphenylmethyl (Tr) substituent we have structurally characterized mono- and ditrityl derivatives of chiral alcohols, amines and amides. During the course of our investigations we have experienced various kinds of packing peculiarities caused by the presence of sterically demanding chiral molecules, e.g. quasi-isomorphism between a pair of enantiomerically pure and racemic crystals, microporosity, lattice inclusion, multiplication of asymmetric units and pseudosymme

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14

Nagae, Haruki, Takahiro Hirai, Daiki Kato, Shusei Soma, Shin-ya Akebi, and Kazushi Mashima. "Dinuclear manganese alkoxide complexes as catalysts for C–N bond cleavage of simple tertiary N,N-dialkylamides to give esters." Chemical Science 10, no. 10 (2019): 2860–68. http://dx.doi.org/10.1039/c8sc05819a.

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Amide bonds are stable due to the resonance between the nitrogen lone pair and the carbonyl moiety, and therefore the chemical transformation of amides, especially tertiary amides, involving C–N bond fission is considered one of the most difficult organic reactions, unavoidably requiring harsh reaction conditions and strong acids or bases.

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15

Eberhardt, Eric S., and Ronald T. Raines. "Amide-Amide and Amide-Water Hydrogen Bonds: Implications for Protein Folding and Stability." Journal of the American Chemical Society 116, no. 5 (1994): 2149–50. http://dx.doi.org/10.1021/ja00084a067.

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16

Szostak, Michal, and Guangchen Li. "Non-Classical Amide Bond Formation: Transamidation and Amidation of Activated Amides and Esters by Selective N–C/O–C Cleavage." Synthesis 52, no. 18 (2020): 2579–99. http://dx.doi.org/10.1055/s-0040-1707101.

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In the past several years, tremendous advances have been made in non-classical routes for amide bond formation that involve transamidation and amidation reactions of activated amides and esters. These new methods enable the formation of extremely valuable amide bonds via transition-metal-catalyzed, transition-metal-free, or metal-free pathways by exploiting chemoselective acyl C–X (X = N, O) cleavage under mild conditions. In a broadest sense, these reactions overcome the formidable challenge of activating C–N/C–O bonds of amides or esters by rationally tackling nN → π*C=O delocalization in am

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17

Bernhardt, Paul V., and Curt Wentrup. "Structures of 4-Iminopyrido[1,2-a]pyrimidines, Pyrido[1,2-a]pyrimidin-4-ones, Pyridopyrimidinium Olates, and Thiazolo[3,2-a]pyrimidine Analogues." Australian Journal of Chemistry 65, no. 4 (2012): 371. http://dx.doi.org/10.1071/ch12040.

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The Structure-Correlation Principle of Bürgi and Dunitz is invoked in an analysis of the structures of 2-chloro-8-methyl-4-(2-(4-picolinyl)imino-4H-pyrido[1,2-a]pyrimidine 8, 7-chloro-5-(2-thiazolyl)imino-5H-thiazolo[3,2-a]pyrimidine 9, 2-methylamino-4H-pyrido[1,2-a]pyrimidin-4-one 10, 7-methylthio-5H-thiazolo[3,2-a]pyrimidin-5-one 11, 2,3-dihydro-7-methylthio-5H-thiazolo[3,2-a]pyrimidin-5-one 12, and 1-methyl-2-[(o-tert-butylphenyl)imino]-1,2-dihydropyrido[1,2-a]pyrimidin-1-ium-4-olate 13, which have been determined by X-ray crystallography. The most notable structural peculiarities are the l

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18

Tan, Ming Yueh, Karen A. Crouse, Thahira B. S. A. Ravoof, Mukesh M. Jotani, and Edward R. T. Tiekink. "3-{(E)-[4-(4-Hydroxy-3-methoxyphenyl)butan-2-ylidene]amino}-1-phenylurea: crystal structure and Hirshfeld surface analysis." Acta Crystallographica Section E Crystallographic Communications 74, no. 1 (2018): 21–27. http://dx.doi.org/10.1107/s2056989017017273.

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Two independent molecules (AandB) comprise the asymmetric unit of the title compound, C18H21N3O3. The urea moiety is disubstituted with one amine being linked to a phenyl ring, which is twisted out of the plane of the CN2O urea core [dihedral angles = 25.57 (11) (A) and 29.13 (10)° (B)]. The second amine is connected to an imine (Econformation), which is linked in turn to an ethane bridge that links a disubstituted benzene ring. Intramolecular amine-N—H...N(imine) and hydroxyl-O—H...O(methoxy) hydrogen bonds closeS(5) loops in each case. The molecules have twisted conformations with the dihedr

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19

V. Komarov, Igor, Aleksandr Yu. Ishchenko, Aleksandr Hovtvianitsa, et al. "Fast Amide Bond Cleavage Assisted by a Secondary Amino and a Carboxyl Group—A Model for yet Unknown Peptidases?" Molecules 24, no. 3 (2019): 572. http://dx.doi.org/10.3390/molecules24030572.

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Unconstrained amides that undergo fast hydrolysis under mild conditions are valuable sources of information about how amide bonds may be activated in enzymatic transformations. We report a compound possessing an unconstrained amide bond surrounded by an amino and a carboxyl group, each mounted in close proximity on a bicyclic scaffold. Fast amide hydrolysis of this model compound was found to depend on the presence of both the amino and carboxyl functions, and to involve a proton transfer in the rate-limiting step. Possible mechanisms for the hydrolytic cleavage and their relevance to peptide

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20

Zhou, Xueer, Petra Vasko, Jamie Hicks, et al. "Cooperative N–H bond activation by amido-Ge(ii) cations." Dalton Transactions 49, no. 27 (2020): 9495–504. http://dx.doi.org/10.1039/d0dt01960g.

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Germylium-ylidene cations, [R(L)Ge]<sup>+</sup>, featuring amido substituents at R and NHC or phosphine donors at L have been synthesized and structurally characterized. The Lewis acidic germanium cation and proximal amide function allow for facile cleavage of N–H bonds in 1,2 fashion.

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21

Hollanders, Karlijn, Bert Maes, and Steven Ballet. "A New Wave of Amide Bond Formations for Peptide Synthesis." Synthesis 51, no. 11 (2019): 2261–77. http://dx.doi.org/10.1055/s-0037-1611773.

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The construction of peptidic amide bonds has become a daily laboratory practice by virtue of well-established ‘coupling reagents’. Nonetheless, inherent limitations connected to these classical coupling methods in terms of waste, safety and expense have yet to be conquered. Research efforts have been devoted to synthetic methods able to surpass these limitations. This short review focuses on the advances made in these ‘non-classical’ methods for amide bond formation with a specific application in peptide chemistry. It consists of two main sections: (i) novel carboxylic activation reagents, and

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22

Hoque, Jiaul, Spandhana Gonuguntla, Venkateswarlu Yarlagadda, Vinod K. Aswal, and Jayanta Haldar. "Effect of amide bonds on the self-assembly of gemini surfactants." Phys. Chem. Chem. Phys. 16, no. 23 (2014): 11279–88. http://dx.doi.org/10.1039/c3cp55244f.

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The effect of amide bonds on micellar aggregation of gemini surfactants was studied by small angle neutron scattering and conductivity methods. The micellar aggregation properties were found to depend strongly on the number and position of amide bonds in the molecules.

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23

Asiri, Abdullah M., Hassan M. Faidallah, Tariq R. Sobahi, Seik Weng Ng, and Edward R. T. Tiekink. "N-(4-Sulfamoylphenyl)acetamide." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (2012): o1155. http://dx.doi.org/10.1107/s1600536812011701.

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In the title compound, C8H10N2O3S, the dihedral angle between the acetamide group and the benzene ring is 15.59 (12)° and the amino group is close to being perpendicular to the benzene ring [N—S—Car—Car(ar = aromatic) torsion angle = 109.4 (2)°]. In the crystal, molecules are linked into supramolecular tubes parallel to [001] by amine–amide N—H...O interactions and these are connected into the three-dimensional architecture by amide–sulfonamide N—H...O hydrogen bonds. The crystal studied was a racemic twin.

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24

Maury, Luc, Joëlle Rambaud, Bernard Pauvert, Yves Lasserre, G. Berge, and Michel Audran. "Étude physico-chimique, spectres de vibration et structure du sulfaméthoxazole." Canadian Journal of Chemistry 63, no. 11 (1985): 3012–18. http://dx.doi.org/10.1139/v85-500.

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Two polymorphic and one solvate forms of sulfamethaxozole have been identified and characterized using various thermal and spectral methods. The crystal structure of form II has been solved and compared with that of form I recently published: the lengths of the intermolecular H bonds mainly differentiate the two polymorphic forms. An assignment of the fundamental vibrations of the amine, amide, and sulfone groups involved in the H intermolecular bonds has been proposed from the analysis of the Raman and infrared spectra.

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25

Viswanathan, Vijayan, Ayyavu Thirunarayanan, Perumal Rajakumar, and Devadasan Velmurugan. "An amide cyclophane." Acta Crystallographica Section E Structure Reports Online 70, no. 8 (2014): o865. http://dx.doi.org/10.1107/s1600536814015621.

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The title compound, 8,18-dithia-2,6-diaza-13(1,4)-piperidina-1(1,2),4(1,3),7(1,2)-tribenzenaoctadecaphane-10,15-diyne-3,6-dione, C32H30N4O2S2, is composed of a relatively planar bis(2-mercaptophenyl)isophthalamide unit linked to a bridging 1,4-di(but-2-yn-1-yl)piperazine unit, forming a macrocycle. The isophthalamide ring is inclined to the outer mercaptophenyl rings by 8.18 (11) and 5.59 (10)°, while these two rings are inclined to one another by 9.10 (12)°. The piperazine ring adopts a chair conformation. There are two intramolecular N—H...S hydrogen bonds generatingS(5) ring motifs. In the

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26

Jan, Chin Yee, Norzianah Binti Haji Shamsudin, Ai Ling Tan, David J. Young, Seik Weng Ng, and Edward R. T. Tiekink. "4-Nitrophthalamide." Acta Crystallographica Section E Structure Reports Online 70, no. 3 (2014): o293. http://dx.doi.org/10.1107/s1600536814002955.

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In the title compound, C8H7N3O4(systematic name: 4-nitrobenzene-1,2-dicarboxamide), each of the substituents is twisted out of the plane of the benzene ring to which it is attached [dihedral angles of 11.36 (2)° for the nitro group, and 60.89 (6) and 34.39 (6)° for the amide groups]. The amide groups are orientated to either side of the least-squares plane through the benzene ring with the amine groups being directed furthest apart. In the crystal, a three-dimensional architecture is established by a network of N—H...O hydrogen bonds.

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27

Kovács, Ervin, Balázs Rózsa, Attila Csomos, Imre Csizmadia, and Zoltán Mucsi. "Amide Activation in Ground and Excited States." Molecules 23, no. 11 (2018): 2859. http://dx.doi.org/10.3390/molecules23112859.

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Not all amide bonds are created equally. The purpose of the present paper is the reinterpretation of the amide group by means of two concepts: amidicity and carbonylicity. These concepts are meant to provide a new viewpoint in defining the stability and reactivity of amides. With the help of simple quantum-chemical calculations, practicing chemists can easily predict the outcome of a desired process. The main benefit of the concepts is their simplicity. They provide intuitive, but quasi-thermodynamic data, making them a practical rule of thumb for routine use. In the current paper we demonstra

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28

Saito, Susumu, Farzaneh Soleymani Movahed, Dinesh N. Sawant, and Dattatraya B. Bagal. "Tris(o-phenylenedioxy)cyclotriphosphazene as a Promoter for the Formation of Amide Bonds Between Aromatic Acids and Amines." Synthesis 52, no. 21 (2020): 3253–62. http://dx.doi.org/10.1055/s-0040-1707174.

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The atom-efficient formation of amide bonds has emerged as a top-priority research field in organic synthesis, as amide bonds constitute the backbones of proteins and represent an important structural motif in drug molecules. Currently, the increasing demand for novel discoveries in this field has focused substantial attention on this challenging subject. Herein, the degradable 1,3,5-triazo-2,4,6-triphosphorine (TAP) motif is presented as a new condensation system for the dehydrative formation of amide bonds between diverse combinations of aromatic carboxylic acids and amines. The underlying r

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29

Maugard, Thierry, Magali Remaud-Simeon, Dominique Petre, and Pierre Monsan. "Enzymatic Synthesis of Surfactants Via Amide Bonds." Biocatalysis and Biotransformation 16, no. 5 (1998): 383–93. http://dx.doi.org/10.3109/10242429809003630.

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30

Müller, Fabian, Monica Trincado, Bruno Pribanic, Matthias Vogt, and Hansjörg Grützmacher. "Stable BH3 adducts to rhodium amide bonds." Journal of Organometallic Chemistry 821 (October 2016): 154–62. http://dx.doi.org/10.1016/j.jorganchem.2016.05.019.

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31

Fan, Liqun, Jinhu Wang, Chunli Liu, et al. "Insight into nucleophilic fragmentation mechanisms by glutamic acid side chain in singly protonated glutathione and related peptidyl ions." European Journal of Mass Spectrometry 26, no. 3 (2019): 175–86. http://dx.doi.org/10.1177/1469066719896708.

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Fragmentation mechanisms of the singly protonated glutathione ( γ-ECG) and its synthetic analogue peptides (ECG and PPECG) have been investigated by liquid chromatography tandem-mass spectrometry and theoretical calculations. In the mass spectra, similar fragmentation patterns were observed for γ-ECG and ECG, but a completely different one was found in the case of PPECG. The E–C amide bond cleavage is the predominant pathway for the fragmentation of γ-ECG and ECG, whereas the additional N-terminal prolyl residues in PPECG significantly suppress the E–C amide bond cleavage. Theoretical calculat

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32

Senior, Levi, and Anthony Linden. "The missing crystal structure in the series of N,N′,N′′-tris(pyridinyl)benzene-1,3,5-tricarboxamides: the 2-pyridinyl derivative." Acta Crystallographica Section E Crystallographic Communications 76, no. 6 (2020): 776–79. http://dx.doi.org/10.1107/s2056989020005599.

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In the first reported crystal structure involving the potential ligand N,N′,N′′-tris(pyridin-2-yl)benzene-1,3,5-tricarboxamide, C24H18N6O3, intermolecular N—H...O hydrogen bonds link the molecules via their amide groups into slanted ladder-like chains, in which the uprights of the ladder are formed by the hydrogen-bonding interactions and the benzene ring cores of the molecules act as the rungs of the ladder. Only two of the three amide groups in the molecule are involved in hydrogen bonding and this influences the degree of out-of-plane twisting at each amide group, with the twist being more

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33

Buchspies, Jonathan, Md Mahbubur Rahman, and Michal Szostak. "Transamidation of Amides and Amidation of Esters by Selective N–C(O)/O–C(O) Cleavage Mediated by Air- and Moisture-Stable Half-Sandwich Nickel(II)–NHC Complexes." Molecules 26, no. 1 (2021): 188. http://dx.doi.org/10.3390/molecules26010188.

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The formation of amide bonds represents one of the most fundamental processes in organic synthesis. Transition-metal-catalyzed activation of acyclic twisted amides has emerged as an increasingly powerful platform in synthesis. Herein, we report the transamidation of N-activated twisted amides by selective N–C(O) cleavage mediated by air- and moisture-stable half-sandwich Ni(II)–NHC (NHC = N-heterocyclic carbenes) complexes. We demonstrate that the readily available cyclopentadienyl complex, [CpNi(IPr)Cl] (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), promotes highly selective transa

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34

Salian, Akshatha R., Sabine Foro, S. Madan Kumar, and B. Thimme Gowda. "Crystal structure and Hirshfeld surface analysis of N,N′-bis(2-nitrophenyl)glutaramide." Acta Crystallographica Section E Crystallographic Communications 74, no. 10 (2018): 1455–59. http://dx.doi.org/10.1107/s2056989018013075.

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The asymmetric unit of the title compound, C17H16N4O6, contains two independent molecules (A and B). The two benzene rings are twisted by an angle of 79.14 (7)° in molecule A, whereas, in molecule B, they are inclined by 19.02 (14)°. The conformations of the molecules are stabilized by intramolecular N—H...O hydrogen bonds between the amide nitrogen atom and the O atom of the ortho-nitro substituent on the phenyl ring, enclosing an S(6) ring motif. In the amide and aliphatic segments, all the N—H, C=O and C—H bonds are anti to each other. In the crystal, the A and B molecules are linked by int

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35

Bergseng, Elin, Jiang Xia, Chu-Young Kim, Chaitan Khosla, and Ludvig M. Sollid. "Main Chain Hydrogen Bond Interactions in the Binding of Proline-rich Gluten Peptides to the Celiac Disease-associated HLA-DQ2 Molecule." Journal of Biological Chemistry 280, no. 23 (2005): 21791–96. http://dx.doi.org/10.1074/jbc.m501558200.

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Binding of peptide epitopes to major histocompatibility complex proteins involves multiple hydrogen bond interactions between the peptide main chain and major histocompatibility complex residues. The crystal structure of HLA-DQ2 complexed with the αI-gliadin epitope (LQPFPQPELPY) revealed four hydrogen bonds between DQ2 and peptide main chain amides. This is remarkable, given that four of the nine core residues in this peptide are proline residues that cannot engage in amide hydrogen bonding. Preserving main chain hydrogen bond interactions despite the presence of multiple proline residues in

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Zarecki, Adam P., Jacek L. Kolanowski, and Wojciech T. Markiewicz. "Microwave-Assisted Catalytic Method for a Green Synthesis of Amides Directly from Amines and Carboxylic Acids." Molecules 25, no. 8 (2020): 1761. http://dx.doi.org/10.3390/molecules25081761.

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Amide bonds are among the most interesting and abundant molecules of life and products of the chemical pharmaceutical industry. In this work, we describe a method of the direct synthesis of amides from carboxylic acids and amines under solvent-free conditions using minute quantities of ceric ammonium nitrate (CAN) as a catalyst. The reactions are carried out in an open microwave reactor and allow the corresponding amides to be obtained in a fast and effective manner when compared to other procedures of the direct synthesis of amides from acids and amines reported so far in the literature. The

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Narayana, B., Prakash S. Nayak, Balladka K. Sarojini, and Jerry P. Jasinski. "4-[(4-Bromophenyl)amino]-2-methylidene-4-oxobutanoic acid." Acta Crystallographica Section E Structure Reports Online 70, no. 7 (2014): o779—o780. http://dx.doi.org/10.1107/s1600536814012872.

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In the title compound, C11H10BrNO3, two independent molecules (AandB) crystallize in the asymmetric unit. The dihedral angles between the mean planes of the 4-bromophenyl ring and amide group are 24.8 (7) in moleculeAand 77.1 (6)° in moleculeB. The mean plane of the methylidene group is further inclined by 75.6 (4) in moleculeAand 72.5 (6)° in moleculeBfrom that of the amide group. In the crystal, N—H...O hydrogen bonds formed by amide groups and O—H...O hydrogen bonds formed by carboxylic acid groups are observed and supported additionally by weak C—H...O interactions between the methylidene

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Chatani, Naoto, Satoshi Inoue, Kazuhiko Yokota, Hiroto Tatamidani, and Yoshiya Fukumoto. "Chelation-assisted carbonylation reactions catalyzed by Rh and Ru complexes." Pure and Applied Chemistry 82, no. 7 (2010): 1443–51. http://dx.doi.org/10.1351/pac-con-09-10-15.

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This account reviews chelation-assisted carbonylation reactions catalyzed by late transition metals. New carbonylation reactions are achieved with these catalysts in the presence of pyridin-2-ylmethanol and pyridin-2-ylmethylamine. The reactions involve activation of O-H and N-H bonds, coordination of the pyridine nitrogen to Rh being essential for the reaction to proceed. In addition, a new type of carbonylation of the ortho C-H bonds in aromatic amides in which the pyridin-2-ylmethylamino moiety functions as a bidentate directing group, is demonstrated. In this reaction, a dinuclear rutheniu

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Borkenhagen, Frank, Ion Neda, Holger Thönnessen, Peter G. Jones, and Reinhard Schmutzler. "Darstellung und Charakterisierung von 2-substituierten 5,6-Benzo-1-methyl- 3-R-1,3,2-diazaphosphorin-4-onen (R = 2-Morpholinoethyl, 1-Adamantyl) mit Phosphor in den Koordinationszahlen drei, vier und fünf / Synthesis and Characterization of 2-Substituted 5 ,6-Benzo-1-methyl-3-R -1,3,2- diazaphosphorin-4-ones (R = 2-Morpholinoethyl, 1-Adamantyl) Containing Phosphorus with Coordination Numbers Three, Four and Five." Zeitschrift für Naturforschung B 51, no. 11 (1996): 1627–38. http://dx.doi.org/10.1515/znb-1996-1117.

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The reaction of N-methylisatoic anhydride with 2-morpholinoethylamine or 1-aminoadamantane furnished N-methyl-N′-(2-morpholinoethyl)anthranilamide 1 and N-methyl-N′- ( l-adamantyl)anthranilamide 2, respectively. 1 and 2 are intermediates in the synthesis of the 2-chloro-3-methyl-1,3,2 λ3-diazaphosphorinones 3 and 4 by reaction of 1 and 2 with PCI3. The reaction of 3 with bis(2-chloroethyl)amine hydrochloride/triethylamine or (2-chloroethyl)amine hydrochloride/triethylamine formed the 2-substituted diazaphosphorinones 5 and 6. Hydrolysis of 3 led to the 2-oxo-λ4P-compound 7. The reaction of 6 w

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Kamanna, Kantharaju, S. Y. Khatavi, and P. B. Hiremath. "Microwave-assisted One-pot Synthesis of Amide Bond using WEB." Current Microwave Chemistry 7, no. 1 (2020): 50–59. http://dx.doi.org/10.2174/2213335606666190828114344.

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Background: Amide bond plays a key role in medicinal chemistry, and the analysis of bioactive molecular database revealed that the carboxamide group appears in more than 25% of the existing database drugs. Typically amide bonds are formed from the union of carboxylic acid and amine; however, the product formation does not occur spontaneously. Several synthetic methods have been reported for amide bond formation in literature. Present work demonstrated simple and eco-friendly amide bond formation using carboxylic acid and primary amines through in situ generation of O-acylurea. The reaction was

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Kaduk, James A., Amy M. Gindhart, and Thomas N. Blanton. "Crystal structure of atazanavir, C38H52N6O7." Powder Diffraction 35, no. 2 (2020): 129–35. http://dx.doi.org/10.1017/s0885715620000135.

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The crystal structure of atazanavir has been solved and refined using synchrotron X-ray powder diffraction data and optimized using density functional techniques. Atazanavir crystallizes in space group P21 (#4) with a = 15.33545(7), b = 5.90396(3), c = 21.56949(13) Å, β = 96.2923(4)°, V = 1941.134(11) Å3, and Z = 2. Despite being labeled as “atazanavir sulfate”, the commercial reagent sample consisted of atazanavir free base. The structure consists of an array of extended-conformation molecules parallel to the ac-plane. Although the atazanavir molecule contains only four classical hydrogen bon

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Orea Flores, Ma Laura, Alberto Galindo Guzmán, Dino Gnecco Medina, and Sylvain Bernès. "N-Benzoyl-N,N′-dicyclohexylurea." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (2006): o2922—o2923. http://dx.doi.org/10.1107/s1600536806022173.

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Bairagi, Keshab M., Katharigatta N. Venugopala, Pradip Kumar Mondal, Bharti Odhav, and Susanta K. Nayak. "Crystal structure of methyl 4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate monohydrate." Acta Crystallographica Section E Crystallographic Communications 72, no. 9 (2016): 1335–38. http://dx.doi.org/10.1107/s2056989016013359.

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The title hydrate, C13H14N2O4·H2O, crystallizes with two formula units in the asymmetric unit (Z′ = 2). The dihedral angles between the planes of the tetrahydropyrimidine ring and the 4-hydroxyphenyl ring and ester group are 86.78 (4) and 6.81 (6)°, respectively, for one molecule and 89.35 (4) and 3.02 (4)° for the other. In the crystal, the organic molecules form a dimer, linked by a pair of N—H...O hydrogen bonds. The hydroxy groups of the organic molecules donate O—H...O hydrogen bonds to water molecules. Further, the hydroxy group accepts N—H...O hydrogen bonds from amides whereas the wate

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Li, Lin, and Jin Kuk Kim. "THERMOREVERSIBLE CROSS-LINKING MALEIC ANHYDRIDE GRAFTED CHLOROBUTYL RUBBER WITH HYDROGEN BONDS (COMBINED WITH IONIC INTERACTIONS)." Rubber Chemistry and Technology 87, no. 3 (2014): 459–70. http://dx.doi.org/10.5254/rct.14.86976.

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ABSTRACT Thermoreversible cross-linking polymers are designed based on reversible cross-linking bonds. These bonds are able to reversibly dissociate and associate upon the input of external energy, such as heat or light. Reprocessibility is possible for this kind of material. The objective was to thermoreversibly cross-link maleic anhydride grafted chlorobutyl rubber (MAH-g-CIIR) via a reaction with octadecylamine, with an excess to obtain amide-salts, which form both hydrogen bonds and ionic interactions. X-ray diffraction experiments showed the presence of microphase-separated aggregates tha

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Tan, Sang Loon, and Edward R. T. Tiekink. "The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study." Acta Crystallographica Section E Crystallographic Communications 76, no. 1 (2020): 102–10. http://dx.doi.org/10.1107/s2056989019016840.

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The crystal and molecular structures of the title 1:2 co-crystal, C14H14N4O2·2C7H6O2, are described. The oxalamide molecule has a (+)-antiperiplanar conformation with the 4-pyridyl residues lying to either side of the central, almost planar C2N2O2 chromophore (r.m.s. deviation = 0.0555 Å). The benzoic acid molecules have equivalent, close to planar conformations [C6/CO2 dihedral angle = 6.33 (14) and 3.43 (10)°]. The formation of hydroxy-O—H...N(pyridyl) hydrogen bonds between the benzoic acid molecules and the pyridyl residues of the diamide leads to a three-molecule aggregate. Centrosymmetri

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Smith, Graham, and Urs D. Wermuth. "Three-dimensional hydrogen-bonded structures in the hydrated proton-transfer salts of isonipecotamide with the dicarboxylic oxalic and adipic acid homologues." Acta Crystallographica Section C Crystal Structure Communications 69, no. 10 (2013): 1192–95. http://dx.doi.org/10.1107/s010827011302430x.

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The structures of the 1:1 hydrated proton-transfer compounds of isonipecotamide (piperidine-4-carboxamide) with oxalic acid, 4-carbamoylpiperidinium hydrogen oxalate dihydrate, C6H13N2O+·C2HO4−·2H2O, (I), and with adipic acid, bis(4-carbamoylpiperidinium) adipate dihydrate, 2C6H13N2O+·C6H8O42−·2H2O, (II), are three-dimensional hydrogen-bonded constructs involving several different types of enlarged water-bridged cyclic associations. In the structure of (I), the oxalate monoanions give head-to-tail carboxylic acid O—H...Ocarboxylhydrogen-bonding interactions, formingC(5) chain substructures whi

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Aakeröy, C. B., and A. M. Beatty. "Low-Dimensional Architectures of Silver Coordination Compounds Assembled via Amide-Amide Hydrogen Bonds." Crystal Engineering 1, no. 1 (1998): 39–49. http://dx.doi.org/10.1016/s0025-5408(98)00033-6.

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Aakeröy, Christer B. "Supramolecular assembly of low-dimensional silver(I) architectures via amide–amide hydrogen bonds." Chemical Communications, no. 10 (1998): 1067–68. http://dx.doi.org/10.1039/a707919b.

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Hudson, Benjamin C., Alessia Battigelli, Michael D. Connolly, et al. "Evidence for cis Amide Bonds in Peptoid Nanosheets." Journal of Physical Chemistry Letters 9, no. 10 (2018): 2574–78. http://dx.doi.org/10.1021/acs.jpclett.8b01040.

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Adams, H., Fiona J. Carver, Christopher A. Hunter, and Nigel J. Osborne. "Amide–aromatic hydrogen-bonds in host–guest recognition." Chem. Commun., no. 22 (1996): 2529–30. http://dx.doi.org/10.1039/cc9960002529.

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