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Journal articles on the topic 'Intramolecular hydrogen transfer'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

Wu, Chia-Hua, Lucas José Karas, Henrik Ottosson, and Judy I.-Chia Wu. "Excited-state proton transfer relieves antiaromaticity in molecules." Proceedings of the National Academy of Sciences 116, no. 41 (September 25, 2019): 20303–8. http://dx.doi.org/10.1073/pnas.1908516116.

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Baird’s rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4n + 2] π-aromatic in the ground state, become [4n + 2] π-antiaromatic in the first 1ππ* states, and proton transfer (either inter- or intramolecularly) helps relieve excited-state antiaromaticity. Computed nucleus-independent chemical shifts (NICS) for several ESPT examples (including excited-state intramolecular proton transfers (ESIPT), biprotonic transfers, dynamic catalyzed transfers, and proton relay transfers) document the important role of excited-state antiaromaticity. o-Salicylic acid undergoes ESPT only in the “antiaromatic” S1 (1ππ*) state, but not in the “aromatic” S2 (1ππ*) state. Stokes’ shifts of structurally related compounds [e.g., derivatives of 2-(2-hydroxyphenyl)benzoxazole and hydrogen-bonded complexes of 2-aminopyridine with protic substrates] vary depending on the antiaromaticity of the photoinduced tautomers. Remarkably, Baird’s rule predicts the effect of light on hydrogen bond strengths; hydrogen bonds that enhance (and reduce) excited-state antiaromaticity in compounds become weakened (and strengthened) upon photoexcitation.

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2

Wang, Se, Zhuang Wang, and Ce Hao. "Role of intramolecular hydrogen bonding in the excited-state intramolecular double proton transfer (ESIDPT) of calix[4]arene: A TDDFT study." Open Physics 14, no. 1 (January 1, 2016): 602–9. http://dx.doi.org/10.1515/phys-2016-0067.

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AbstractThe time-dependent density functional theory (TDDFT) method was performed to investigate the excited-state intramolecular double proton transfer (ESIDPT) reaction of calix[4]arene (C4A) and the role of the intramolecular hydrogen bonds in the ESIDPT process. The geometries of C4A in the ground state and excited states (S1, S2 and T1) were optimized. Four intramolecular hydrogen bonds formed in the C4A are strengthened or weakened in the S2 and T1 states compared to those in the ground state. Interestingly, upon excitation to the S1 state of C4A, two protons H1 and H2 transfer along the two intramolecular hydrogen bonds O1-H1···O2 and O2-H2···O3, while the other two protons do not transfer. The ESIDPT reaction breaks the primary symmetry of C4A in the ground state. The potential energy curves of proton transfer demonstrate that the ESIDPT process follows the stepwise mechanism but not the concerted mechanism. Findings indicate that intramolecular hydrogen bonding is critical to the ESIDPT reactions in intramolecular hydrogen-bonded systems.

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3

Miesen, Franciscus W. A. M., Hans C. M. Baeten, Harm A. Langermans, Leo H. Koole, and Henk A. Claessens. "Novel, intramolecular hydrogen-transfer and cyclo-addition photochemistry of cyclic 1,3-dienes." Canadian Journal of Chemistry 69, no. 10 (October 1, 1991): 1554–62. http://dx.doi.org/10.1139/v91-230.

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With use of one- and two-dimensional NMR spectroscopy and deuterium labelling, the photochemistry of 9-endo-hydroxy-9-exo-vinyl-bicyclo[4.2.1]nonadiene (1) and the 9-exo-(11-dimethylvinyl)- (2) and 9-exo-ethyl- (3) analogues has been studied. Irradiation of 1–3 gave novel 8-membered ring systems 4–6 by a light-induced rearrangement process, in which the hydroxyl proton is transferred on one side of the molecule toward one of the termini of the endocyclic diene. This rearrangement process thus involves a formal hydrogen transfer, during which either H+ or H• may be transferred to a reactive diene intermediate. Replacement of the hydroxyl proton by deuterium in 1–3, and 2H NMR of the corresponding photoproducts, confirmed that the hydrogen translocation occurs intramolecularly. Prolonged irradiation of 4 and 5 results in the formation of pyran products 10 and 11 by an intramolecular photocycloaddition of the triplet excited state of the α,β-unsaturated ketone to 1,3-cis,cis-cyclooctadiene, via a stabilized bisallylic biradical intermediate. Conformational studies of the structurally more rigid system 10, which is derived from 4, revealed that the hydroxyl proton was transferred on the endo side of the molecule. Key words: intramolecular hydrogen transfer, photochemistry of hydroxy-alkyl-bicyclononadienes, intramolecular photocycloaddition, conformational studies.

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4

Schaub, Thomas, Stefan Rüdenauer, and Martine Weis. "Intramolecular Hydrogen Transfer Reaction: Menthon from Isopulegol." Organic Letters 16, no. 10 (April 29, 2014): 2575–77. http://dx.doi.org/10.1021/ol500811u.

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5

Harada, Takaaki, Stephen F. Lincoln, and Tak W. Kee. "Excited-state dynamics of the medicinal pigment curcumin in a hydrogel." Physical Chemistry Chemical Physics 18, no. 40 (2016): 28125–33. http://dx.doi.org/10.1039/c6cp05648b.

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Curcumin is a yellow polyphenol with multiple medicinal effects. We show that excited-state intramolecular hydrogen atom transfer and solvent reorganisation are major photophysical events for curcumin in the PAAC18 hydrogel.

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6

Nielsen, Michael L., Bogdan A. Budnik, Kim F. Haselmann, Jesper V. Olsen, and Roman A. Zubarev. "Intramolecular hydrogen atom transfer in hydrogen-deficient polypeptide radical cations." Chemical Physics Letters 330, no. 5-6 (November 2000): 558–62. http://dx.doi.org/10.1016/s0009-2614(00)01078-2.

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7

Herrmann, Hendrik, Elisabeth Kaifer, and Hans‐Jörg Himmel. "Hydrogen‐Atom Transfer (HAT) Initiated by Intramolecular Ligand–Metal Electron Transfer." Chemistry – A European Journal 23, no. 23 (April 4, 2017): 5520–28. http://dx.doi.org/10.1002/chem.201605971.

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8

Takahashi, Hiroaki, Yoshiki Watanabe, Makoto Sakai, and Masanori Tachikawa. "Photoinduced Intramolecular Hydrogen Transfer Reaction of Ortho Nitrobenzyl Compounds." Laser Chemistry 19, no. 1-4 (January 1, 1999): 357–62. http://dx.doi.org/10.1155/1999/29456.

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Time-resolved resonance Raman and absorption spectra have revealed that the photoinduced intramolecular hydrogen transfer reaction of ortho nitrobenzyl compounds is initiated by the abstraction of methylene hydrogen by the ortho nitro group to generate the ortho aci-nitro acid isomer. In polar solvents the ortho aci-nitro acid is dissociated into the aci-nitro anion and a proton, and the proton is captured by other hydrogen accepting sites, such as 2-pyridyl, 4-pyridyl and 4-nitro groups to generate the ortho N—H quinoid, para N—H quinoid and para aci-nitro acid isomers, respectively. For 2-nitroethylbenzene and 2- and 4-(2′-nitrobenzyl)pyridines the structure of the aci-nitro anion is very similar to that of their respective ortho aci-nitro acid, while for 2,4-dinitroethylbenzene the structure of the aci-nitro anion quite resembles that of the para aci-nitro acid.

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9

Spiegel, Maciej, Tadeusz Andruniów, and Zbigniew Sroka. "Flavones’ and Flavonols’ Antiradical Structure–Activity Relationship—A Quantum Chemical Study." Antioxidants 9, no. 6 (May 27, 2020): 461. http://dx.doi.org/10.3390/antiox9060461.

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Flavonoids are known for their antiradical capacity, and this ability is strongly structure-dependent. In this research, the activity of flavones and flavonols in a water solvent was studied with the density functional theory methods. These included examination of flavonoids’ molecular and radical structures with natural bonding orbitals analysis, spin density analysis and frontier molecular orbitals theory. Calculations of determinants were performed: specific, for the three possible mechanisms of action—hydrogen atom transfer (HAT), electron transfer–proton transfer (ETPT) and sequential proton loss electron transfer (SPLET); and the unspecific—reorganization enthalpy (RE) and hydrogen abstraction enthalpy (HAE). Intramolecular hydrogen bonding, catechol moiety activity and the probability of electron density swap between rings were all established. Hydrogen bonding seems to be much more important than the conjugation effect, because some structures tends to form more intramolecular hydrogen bonds instead of being completely planar. The very first hydrogen abstraction mechanism in a water solvent is SPLET, and the most privileged abstraction site, indicated by HAE, can be associated with the C3 hydroxyl group of flavonols and C4’ hydroxyl group of flavones. For the catechol moiety, an intramolecular reorganization to an o-benzoquinone-like structure occurs, and the ETPT is favored as the second abstraction mechanism.

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10

Förster, Christoph, Philipp Veit, Vadim Ksenofontov, and Katja Heinze. "Diferrocenyl tosyl hydrazone with an ultrastrong NH⋯Fe hydrogen bond as double click switch." Chemical Communications 51, no. 8 (2015): 1514–16. http://dx.doi.org/10.1039/c4cc08868a.

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The intramolecular NH⋯Fe hydrogen bond in diferrocenyl hydrazone 2 raises the barrier for intramolecular electron transfer in its mixed-valent cation 2+ and is only disrupted by double oxidation to 22+.

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11

Nagib, David, Leah Stateman, and Kohki Nakafuku. "Remote C–H Functionalization via Selective Hydrogen Atom Transfer." Synthesis 50, no. 08 (February 12, 2018): 1569–86. http://dx.doi.org/10.1055/s-0036-1591930.

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The selective functionalization of remote C–H bonds via intramolecular hydrogen atom transfer (HAT) is transformative for organic synthesis. This radical-mediated strategy provides access to novel reactivity that is complementary to closed-shell pathways. As modern methods for mild generation of radicals are continually developed, inherent selectivity paradigms of HAT mechanisms offer unparalleled opportunities for developing new strategies for C–H functionalization. This review outlines the history, recent advances, and mechanistic underpinnings of intramolecular HAT as a guide to addressing ongoing challenges in this arena.1 Introduction2 Nitrogen-Centered Radicals2.1 sp3 N-Radical Initiation2.2 sp2 N-Radical Initiation3 Oxygen-Centered Radicals3.1 Carbonyl Diradical Initiation3.2 Alkoxy Radical Initiation3.3 Non-alkoxy Radical Initiation4 Carbon-Centered Radicals4.1 sp2 C-Radical Initiation4.2 sp3 C-Radical Initiation5 Conclusion

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12

Ohta, Y., T. Yoshimoto, and K. Nishikawa. "One approach to the control of intramolecular hydrogen transfer." Chemical Physics Letters 316, no. 5-6 (January 2000): 551–57. http://dx.doi.org/10.1016/s0009-2614(99)01317-2.

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13

Sordo, T. L., and J. J. Dannenberg. "Intramolecular Aromatic 1,5-Hydrogen Transfer in Free Radical Systems." Journal of Organic Chemistry 64, no. 6 (March 1999): 1922–24. http://dx.doi.org/10.1021/jo981961n.

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14

Simkovitch, Ron, and Dan Huppert. "Intramolecular Excited-State Hydrogen Transfer in Rutin and Quercetin." Israel Journal of Chemistry 57, no. 5 (January 20, 2017): 393–402. http://dx.doi.org/10.1002/ijch.201600112.

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15

Zhang, Fengjin, Di Zhang, Yong Du, Peipei Jin, Yanying Zhao, Xuming Zheng, and Jiadan Xue. "Direct observation of stepwise intermolecular proton and hydrogen transfer between alcohols and the triplet state of 4-nitro-1-naphthol." Physical Chemistry Chemical Physics 20, no. 17 (2018): 11876–81. http://dx.doi.org/10.1039/c8cp00484f.

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Solvent assisted excited state intramolecular proton or hydrogen transfer has received much attention in bi-functional molecules with hydrogen donating and hydrogen accepting groups. Whether this takes place in 4-nitro-1-naphtol was examined in this work.

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16

Wei, Qiang, Jiyu Wang, Meiyu Zhao, Meixia Zhang, Yuzhi Song, and Peng Song. "A theoretical investigation on excited-state single or double proton transfer process for aloesaponarin I." Canadian Journal of Chemistry 96, no. 1 (January 2018): 83–88. http://dx.doi.org/10.1139/cjc-2017-0533.

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The excited-state proton transfer (ESPT) dynamical behavior of aloesaponarin I (ASI) was studied using density functional theory (DFT) and time-dependent DFT (TDDFT) methods. Our calculated vertical excitation energies based on TDDFT reproduced the experimental absorption and fluorescence spectra well [Nagaoka et al. J. Phys. Chem. B, 117, 4347 (2013)]. Two intramolecular hydrogen bonds were confirmed to be strengthened in the S1 state, which makes ESPT possible. Herein, the ESPT process is more likely to happen, along with one hydrogen bond (O1–H2⋯O3). Qualitative analyses about charge distribution further demonstrate that the ESPT process could occur because of the intramolecular charge transfer. Our constructed potential energy surfaces of both S0 and S1 states show that a single proton transfer reactive is more reasonable along with the intramolecular hydrogen bond (O1–H2⋯O3) rather than O4–H5⋯O6 in the S1 stated potential energy surface. Then, ASI-SPT* decays to the ground state with a 640 nm fluorescence; subsequently, the ASI-SPT form shows that reverse ground state single-proton transfer back to the ASI structure occurs. Particularly, dependent on relatively accurate potential energy barriers among these excited-state stable structures, we confirmed the excited-state single proton transfer process rather than using the controversial nodal plane model.

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17

Rinne, Benjamin L., A. Paige Lathem, and Zachariah M. Heiden. "Influence of intramolecular vs. intermolecular phosphonium-borohydrides in catalytic hydrogen, hydride, and proton transfer reactions." Dalton Transactions 46, no. 29 (2017): 9382–93. http://dx.doi.org/10.1039/c7dt01693j.

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18

Wang, Qin, Yahui Niu, Rong Wang, Haoran Wu, and Yanrong Zhang. "Acid‐Induced Shift of Intramolecular Hydrogen Bonding Responsible for Excited‐State Intramolecular Proton Transfer." Chemistry – An Asian Journal 13, no. 13 (May 30, 2018): 1735–43. http://dx.doi.org/10.1002/asia.201800457.

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19

Hu, Shanshan, Kun Liu, Yuanzuo Li, Qianqian Ding, Wei Peng, and Maodu Chen. "Investigation of excited-state intramolecular proton transfer coupled charge transfer reaction of paeonol." Canadian Journal of Chemistry 92, no. 4 (April 2014): 274–78. http://dx.doi.org/10.1139/cjc-2013-0286.

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An excited-state intramolecular proton transfer (ESIPT) coupled charge transfer reaction of paeonol was investigated both experimentally and theoretically. The ESIPT reaction of paeonol was predicted based on the large Stokes shift, which is observed in steady-state absorption and fluorescence spectra in an ethanol solution. The steady-state spectra in some solutions, such as methanol, ethanol, propanol, dichloromethane, and n-hexane, illustrate that the ESIPT reaction of paeonol has no dependence on the solvent properties. Therefore, the excited-state intermolecular proton transfer cannot be generated in protic solvents. Using the density functional theory and time-dependent density functional theory methods, we make a subsequent theoretical calculation that indicates that the ESIPT reaction of paeonol occurs through the intramolecular hydrogen bond O−H···O=C. The excited-state potential energy curve of paeonol indicates that the ESIPT reaction is a barrierless process, and the fluorescence emission of paeonol at 493 nm in the ethanol solution was assigned to the keto isomer fluorescence. Additionally, we also found an intramolecular charge transfer in the excited state by analysing the frontier molecular orbitals of paeonol.

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20

Dux, R., KP Ghiggino, and O. Vogl. "Photochemical Processes in a Copolymer of 2-(2'-Hydroxy-4'-methacryloyloxyphenyl)-2H-benzotriazole and Methyl Methacrylate." Australian Journal of Chemistry 47, no. 8 (1994): 1461. http://dx.doi.org/10.1071/ch9941461.

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The temperature-dependent (10-300 K) fluorescence behaviour of films of a copolymer of 2-(2′-hydroxy-4′-methacryloyloxyphenyl)-2H-benzotriazole and methyl methacrylate (HMPB-co-MMA) has been studied. The emission spectra consist of a short-wavelength band and a highly Stokes-shifted emission with maxima at 390 and 550 nm respectively. The temperature- insensitive 390 nm emission is assigned to a non- intramolecular hydrogen-bonded form of HMPB while the red-shifted emission is due to the species formed following excited-state intramolecular proton transfer. The temperature dependence of the 550 nm fluorescence is complex and does not allow a linear Arrhenius plot. Possible mechanisms for the temperature-dependent deactivation processes are proposed. Irradiation studies indicate that the non-planar HMPB entities are more photolabile than the intramolecularly hydrogen-bonded form. The relevance of the results to the application of HMPB as an ultraviolet absorber and photostabilizer in polymers is discussed.

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21

Kirby, Anthony J., José Carlos Gesser, Florian Hollfelder, Jacks P. Priebe, and Faruk Nome. "Intramolecular general acid catalysis of sulfate transfer Nucleophilic attack by oxyanions on the SO3 group." Canadian Journal of Chemistry 83, no. 9 (September 1, 2005): 1629–36. http://dx.doi.org/10.1139/v05-172.

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The mechanism of hydrolysis of 8-N,N-dimethylaminonaphthyl sulfate closely resembles that of the corresponding phosphate monoester. Nucleophilic attack by water on the sulfate group of the zwitterion is catalyzed by the neighbouring dimethylammonium group, acting as a particularly efficient general acid through the intramolecular hydrogen bond. This hydrogen bond is present in both reactant and product, but is strongest in the transition state. Transfer of the sulfuryl group to oxygen nucleophiles, including water and carboxylate anions, shows steric and electrostatic effects, and a sensitivity to basicity which is low, but significantly higher than expected for uncatalyzed transfer of the SO3 group.Key words: sulfate, sulfatase, intramolecular, general acid catalysis, promiscuity.

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22

Wang, Na, Liu Ye, Zhong-Liang Li, Lei Li, Zhuang Li, Hong-Xia Zhang, Zhen Guo, Qiang-Shuai Gu, and Xin-Yuan Liu. "Hydrofunctionalization of alkenols triggered by the addition of diverse radicals to unactivated alkenes and subsequent remote hydrogen atom translocation." Organic Chemistry Frontiers 5, no. 19 (2018): 2810–14. http://dx.doi.org/10.1039/c8qo00734a.

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23

Kalaiselvan, Arumugan, Aswini Spergen, Isukapalli Sai Vamsi Krishna, Vennapusa Sivaranjana Reddy, and Sabapathi Gokulnath. "Double intramolecular hydrogen transfer assisted dual emission in a carbazole-embedded porphyrin-like macrocycle." Chemical Communications 57, no. 36 (2021): 4420–23. http://dx.doi.org/10.1039/d1cc00868d.

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Carbazole-embedded porphyrin-like macrocycle 3, bearing a meso-pyrrole substituent, exhibits dual fluorescence. Photophysical studies reveal two distinguishable NH-tautomers arising through double intramolecular hydrogen transfer.

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24

Najafi, Meysam, and Syed Ali Raza Naqvi. "Theoretical study of the substituent effect on the hydrogen atom transfer mechanism of the irigenin derivatives antioxidant action." Journal of Theoretical and Computational Chemistry 13, no. 02 (March 2014): 1450010. http://dx.doi.org/10.1142/s0219633614500102.

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In this paper, 21 substituents with various electron donating and electron withdrawing characters were placed in available positions of irigenin in order to study their effect on the O – H bond dissociation enthalpy (BDE) via DFT/B3LYP method. Results indicated the substituents in X3 and X4 positions have exerted stronger influence upon BDE values of irigenin derivatives when compared with same substituents in X1 and X2 positions. The results show that intramolecular hydrogen bond effects are able to considerably stabilize the parents and radicals. The natural bond orbital (NBO) analysis results also confirmed the intramolecular hydrogen bond stabilization. The formation of strong intramolecular hydrogen bonds in several radicals results in low BDEs. The 3- OH BDE values for substituents in X2 position have linear dependencies with Hammett constants (Fig. 2 and Eq. (2)). Found dependencies are suitably linear, that can be important for the synthesis of novel antioxidants based on irigenin.

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25

Bourgeois, Marie-Josèphe, Marianne Vialemaringe, Monique Campagnole, and Evelyne Montaudon. "Réaction compétitive de la substitution homolytique intramoléculaire : décomposition de peroxydes allyliques dans le thioglycolate de méthyle." Canadian Journal of Chemistry 79, no. 3 (March 1, 2001): 257–62. http://dx.doi.org/10.1139/v01-024.

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The decomposition of allylic peroxides in methyl thioglycolate always leads to both epoxide and adduct peroxide. According to the nature of the allylic chain, either epoxide or peroxide is the predominant product, if not the only one. It is the first example where the hydrogen transfer is as fast as the intramolecular homolytic substitution. The influence of different factors upon the competition is studied.Key words: allylic peroxides, epoxides, intramolecular homolytic substitution, transfer.

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26

Hoshino, Osamu, Miyuki Ishizaki, and Hideaki Takano. "Intramolecular 1,5-Hydrogen Atom Transfer Radical Reaction of Pyrrolidine Derivatives." HETEROCYCLES 49, no. 1 (1998): 305. http://dx.doi.org/10.3987/com-98-s34.

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27

Mandado, Marcos, Ricardo A. Mosquera, Ana M. Graña, and Christian Van Alsenoy. "Charge density analysis of some processes involving intramolecular hydrogen transfer." Tetrahedron 61, no. 4 (January 2005): 819–29. http://dx.doi.org/10.1016/j.tet.2004.11.044.

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28

Curran, Dennis P., Dooseop Kim, Hong Tao Liu, and Wang Shen. "Translocation of radical sites by intramolecular 1,5-hydrogen atom transfer." Journal of the American Chemical Society 110, no. 17 (August 1988): 5900–5902. http://dx.doi.org/10.1021/ja00225a052.

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29

Liu, Wei, Hong-Yu Zhang, De-Zhan Chen, Zhi-Yi Zhang, and Man-Hua Zhang. "Theoretical study on intramolecular hydrogen transfer involving amino-substituted perylenequinone." Dyes and Pigments 47, no. 3 (December 2000): 277–84. http://dx.doi.org/10.1016/s0143-7208(00)00084-x.

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30

Kong, Ling, K. Indira Priyadarsini, and Hong-Yu Zhang. "A theoretical investigation on intramolecular hydrogen-atom transfer in curcumin." Journal of Molecular Structure: THEOCHEM 684, no. 1-3 (September 2004): 111–16. http://dx.doi.org/10.1016/j.theochem.2004.06.034.

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31

Yang, Hsiao-Chuan, Hui-Lung Chen, and Jia-Jen Ho. "Ab initio study of intramolecular hydrogen transfer in formylperoxy radical." Journal of Molecular Structure: THEOCHEM 774, no. 1-3 (November 2006): 35–41. http://dx.doi.org/10.1016/j.theochem.2006.07.003.

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32

Lee, Hanleem, Sora Bak, Yunhee Cho, Meeree Kim, Se Hwang Kang, Viet Q. Bui, Hung M. Le, Sung Wng Kim, and Hyoyoung Lee. "Hydrogen adsorption engineering by intramolecular proton transfer on 2D nanosheets." NPG Asia Materials 10, no. 5 (May 2018): 441–54. http://dx.doi.org/10.1038/s41427-018-0037-2.

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33

Gu, Yanan, Han Shen, and Yongjun Li. "Tuning Intramolecular Charge Transfer through Adjusting Hydrogen Bonding by Anions." Asian Journal of Organic Chemistry 9, no. 2 (February 2020): 303–10. http://dx.doi.org/10.1002/ajoc.201900713.

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34

Schöneich, Christian, Olivier Mozziconacci, Willem H. Koppenol, and Thomas Nauser. "Intramolecular 1,2- and 1,3-Hydrogen Transfer Reactions of Thiyl Radicals." Israel Journal of Chemistry 54, no. 3 (March 2014): 265–71. http://dx.doi.org/10.1002/ijch.201300107.

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35

Matsuzawa, Hideyo, Takashi Nakagaki, and Makio Iwahashi. "Intramolecular Hydrogen Bonding (Proton Transfer) of 1-Phenyl-1,3-butanedione." Journal of Oleo Science 56, no. 12 (2007): 653–58. http://dx.doi.org/10.5650/jos.56.653.

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36

Carrington, Tucker, and William H. Miller. "Reaction surface description of intramolecular hydrogen atom transfer in malonaldehyde." Journal of Chemical Physics 84, no. 8 (April 15, 1986): 4364–70. http://dx.doi.org/10.1063/1.450058.

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37

Trimarchi, Michaeleen C. L., Mark A. Green, John C. Huffman, and Kenneth G. Caulton. "Photoinitiated intramolecular hydrogen transfer from rhenium polyhydrides to C8 cyclopolyolefins." Organometallics 4, no. 3 (March 1985): 514–19. http://dx.doi.org/10.1021/om00122a014.

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38

Pan, Yang, Lidong Zhang, Taichang Zhang, Huijun Guo, Xin Hong, Liusi Sheng, and Fei Qi. "Intramolecular hydrogen transfer in the ionization process of α-alanine." Physical Chemistry Chemical Physics 11, no. 8 (2009): 1189. http://dx.doi.org/10.1039/b813268b.

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39

Moran, Damian, Rebecca Jacob, Geoffrey P F. Wood, Michelle L Coote, Michael J Davies, Richard A J. O'Hair, Christopher J Easton, and Leo Radom. "Rearrangements in Model Peptide-Type Radicalsvia Intramolecular Hydrogen-Atom Transfer." Helvetica Chimica Acta 89, no. 10 (October 2006): 2254–72. http://dx.doi.org/10.1002/hlca.200690210.

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40

Wang, Dinghai, Kalipada Jana, and Armido Studer. "Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes." Organic Letters 23, no. 15 (July 14, 2021): 5876–79. http://dx.doi.org/10.1021/acs.orglett.1c01998.

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41

Xu, Pengfei, Tang Gao, Meihui Liu, Hailiang Zhang, and Wenbin Zeng. "A novel excited-state intramolecular proton transfer (ESIPT) dye with unique near-IR keto emission and its application in detection of hydrogen sulfide." Analyst 140, no. 6 (2015): 1814–16. http://dx.doi.org/10.1039/c4an02285h.

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42

Zhang, Zhiyun, Yen-Hao Hsu, Yi-An Chen, Chi-Lin Chen, Tzu-Chieh Lin, Jiun-Yi Shen, and Pi-Tai Chou. "New six- and seven-membered ring pyrrole–pyridine hydrogen bond systems undergoing excited-state intramolecular proton transfer." Chem. Commun. 50, no. 95 (2014): 15026–29. http://dx.doi.org/10.1039/c4cc07109c.

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43

Schöneich, Christian. "Cysteine residues as catalysts for covalent peptide and protein modification: a role for thiyl radicals?" Biochemical Society Transactions 39, no. 5 (September 21, 2011): 1254–59. http://dx.doi.org/10.1042/bst0391254.

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Cysteine thiyl radicals engage in reversible intramolecular hydrogen-transfer reactions with amino acid residues in peptides and proteins. These reactions can be experimentally demonstrated through covalent hydrogen–deuterium exchange when experiments are carried out in 2H2O. To this end, hydrogen-transfer reactions have been observed between cysteine thiyl radicals and glycine, alanine, serine, valine and leucine in both model peptides and a protein, insulin. The relevance of such reactions for protein oxidation under conditions of oxidative stress is discussed.

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44

Sun, Dongjie, Jinghai Fang, Guanghua Yu, and Fengcai Ma. "Intramolecular hydrogen bonding and photoinduced intramolecular proton and electron transfer in 2-(2′-hydroxyphenyl)benzothiazole." Journal of Molecular Structure: THEOCHEM 806, no. 1-3 (March 2007): 105–12. http://dx.doi.org/10.1016/j.theochem.2006.11.015.

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Bártová, Kateřina, Lucie Čechová, Eliška Procházková, Ondřej Socha, Zlatko Janeba, and Martin Dračínský. "Influence of Intramolecular Charge Transfer and Nuclear Quantum Effects on Intramolecular Hydrogen Bonds in Azopyrimidines." Journal of Organic Chemistry 82, no. 19 (September 8, 2017): 10350–59. http://dx.doi.org/10.1021/acs.joc.7b01810.

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46

Sarkar, Sumon, Kelvin Pak Shing Cheung, and Vladimir Gevorgyan. "C–H functionalization reactions enabled by hydrogen atom transfer to carbon-centered radicals." Chemical Science 11, no. 48 (2020): 12974–93. http://dx.doi.org/10.1039/d0sc04881j.

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Khalafy, Jabbar, and Rolf H. Prager. "Flash Vacuum Pyrolysis of Some N-Benzylbenzotriazoles and N-Benzylbenzisoxazolones." Australian Journal of Chemistry 51, no. 10 (1998): 925. http://dx.doi.org/10.1071/c98065.

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The flash vacuum pyrolysis products of 2-(benzotriazol-1-ylmethyl)benzonitrile, methyl 2-(benzotriazol-1-ylmethyl)benzoate and the corresponding benzisoxazolones have been characterized. The benzotriazoles lose nitrogen to give diradicals which undergo intramolecular hydrogen-atom transfer or cyclization, while the benzisoxazolones rearrange initially to the corresponding benzaldehyde N-(2-carboxyphenyl)imines which undergo subsequent intramolecular addition reactions.

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48

Chen, Hui, and Shouyun Yu. "Remote C–C bond formation via visible light photoredox-catalyzed intramolecular hydrogen atom transfer." Organic & Biomolecular Chemistry 18, no. 24 (2020): 4519–32. http://dx.doi.org/10.1039/d0ob00854k.

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Visible light photoredox catalysis combined with intramolecular hydrogen atom transfer (HAT) can serve as a unique tool for achieving remote C–C bond formation. Recent advances in photoredox-catalyzed remote C–C bond formation are summarized.

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49

Bosch, Enric, Miquel Moreno, and José María Lluch. "The role of coupling in intramolecular proton transfer reactions. The hydrogen oxalate anion as an example." Canadian Journal of Chemistry 70, no. 1 (January 1, 1992): 100–106. http://dx.doi.org/10.1139/v92-017.

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Coupling between the proton motion and the internal degrees of freedom for intramolecular proton transfer in the hydrogen oxalate anion has been studied. A normal mode analysis at a sequence of points along the Intrinsic Reaction Coordinate (IRC) has been performed and the coupling functions Bk.F have been obtained. It is shown that, although for the reactant the IRC direction essentially consists of the motion of oxygen atoms, the coupling changes this IRC direction towards the motion corresponding to proton transfer itself. From a quantum point of view, the curvature that appears as a consequence allows comer-cutting tunneling. Finally, the effect of isotope substitution is considered. Keywords: intramolecular proton transfer, coupling functions, IRC curvature, tunneling splitting, isotope substitution.

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50

Gutiérrez-Arzaluz, Luis, Fernando Cortés-Guzmán, Tomás Rocha-Rinza, and Jorge Peón. "Ultrafast excited state hydrogen atom transfer in salicylideneaniline driven by changes in aromaticity." Physical Chemistry Chemical Physics 17, no. 47 (2015): 31608–12. http://dx.doi.org/10.1039/c5cp03699b.

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Quantum chemical topology shows that (i) the ultrafast excited state intramolecular proton transfer in salicylideneaniline occurs after considerable loss in aromaticity upon photoexcitation and (ii) the transferred species has a charge intermediate between that in a bare proton and a neutral hydrogen atom.

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