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1

Saha, Subhankar, Somnath Ganguly, and Gautam R. Desiraju. "Graded IR Filters: Distinguishing Between Single and Multipoint NO2···I Halogen Bonded Supramolecular Synthons (P, Q, and R Synthons)." Australian Journal of Chemistry 67, no. 12 (2014): 1840. http://dx.doi.org/10.1071/ch14361.

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The NO2···I supramolecular synthon is a halogen bonded recognition pattern that is present in the crystal structures of many compounds that contain these functional groups. These synthons have been previously distinguished as P, Q, and R types using topological and geometrical criteria. A five step IR spectroscopic sequence is proposed here to distinguish between these synthon types in solid samples. Sets of known compounds that contain the P, Q, and R synthons are first taken to develop IR spectroscopic identifiers for them. The identifiers are then used to create graded IR filters that sieve
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2

Saha, Subhankar, Lalit Rajput, Sumy Joseph, Manish Kumar Mishra, Somnath Ganguly, and Gautam R. Desiraju. "IR spectroscopy as a probe for C–H⋯X hydrogen bonded supramolecular synthons." CrystEngComm 17, no. 6 (2015): 1273–90. http://dx.doi.org/10.1039/c4ce02034k.

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3

Koča, Jaroslav. "A mathematical model of the synthon." Collection of Czechoslovak Chemical Communications 53, no. 5 (1988): 1007–17. http://dx.doi.org/10.1135/cccc19881007.

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A mathematical model of the synthon is suggested. The term synthon is used to denote one or several molecules or their part(s) with free valences. The notion of isomeric synthons on a set of atoms A and that of the Family of Isomeric Synthons FIS(A) are introduced. Matrix operators are defined for modelling the elementary steps of reorganization of electrons during reactions. A new notion of the reaction distance of isomeric synthons is introduced as the smallest number of elementary steps of reorganization of electrons during the reaction transforming one synthon into another.
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4

Torubaev, Yury V. "Chimeric supramolecular synthons in Ph2Te2(I2)Se." Acta Crystallographica Section C Structural Chemistry 76, no. 6 (2020): 579–84. http://dx.doi.org/10.1107/s2053229620006166.

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Iodination of Ph2Te2Se by molecular iodine is directed towards the Te atom and yields {diiodo[(phenyltellanyl)selanyl]-λ4-tellanyl}benzene, PhTeSeTeI2Ph or C12H10I2SeTe2. The molecule can be considered as a chimera of PhTeSeR, PhTeSeTePh and R′TeI2Ph fragments. The crystal structure features a complex interplay of the supramolecular synthons Te...π(Ph), Se...Te and I...Te, combining molecules into a three-dimensional framework. Their combination affords long-range supramolecular synthons which are fused in a way resembling the mythological chimera and could be defined as chimeric supramolecula
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5

Bolla, Geetha, and Ashwini Nangia. "Supramolecular synthon hierarchy in sulfonamide cocrystals with syn-amides and N-oxides." IUCrJ 6, no. 4 (2019): 751–60. http://dx.doi.org/10.1107/s2052252519005037.

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Sulfonamide drugs are well known antibacterial and antimicrobial molecules for pharmaceutical development. Building a library of suitable supramolecular synthons for the sulfonamide functional group and understanding their crystal structures with partner coformer molecules continues to be a challenge in crystal engineering. Although a few sulfonamide cocrystals with amides and N-oxides have been reported, the body of work on sulfonamide synthons is limited compared with those that have carboxylic acids and carboxamides. To address this structural gap, the present work is primarily focused on s
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6

Mendoza-Meroño, Rafael, and Santiago García-Granda. "(1E,2E)-2-Methyl-3-phenylacrylaldehyde thiosemicarbazone." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1840. http://dx.doi.org/10.1107/s1600536812022386.

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In the crystal structure of the title compound, C11H13N3S, molecules form centrosymmetric synthons with an R 2 2(8) graph-set motif, linked by pairs of N—H...S hydrogen bonds. The synthons are connected through further N—H...S hydrogen bonds, extending the packing to form a two-dimensional network lying parallel to (001). In addition, C—H...π interactions are observed.
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7

Cai, Linhong, Lan Jiang, Cong Li, Xiaoshu Guan, Li Zhang, and Xiangnan Hu. "Multicomponent Crystal of Metformin and Barbital: Design, Crystal Structure Analysis and Characterization." Molecules 26, no. 14 (2021): 4377. http://dx.doi.org/10.3390/molecules26144377.

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The formation of most multicomponent crystals relies on the interaction of hydrogen bonds between the components, so rational crystal design based on the expected hydrogen-bonded supramolecular synthons was employed to establish supramolecular compounds with desirable properties. This theory was put into practice for metformin to participate in more therapeutic fields to search for a fast and simple approach for the screening of candidate crystal co-formers. The prediction of intermolecular synthons facilitated the successful synthesis of a new multicomponent crystal of metformin (Met) and bar
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8

Koval', I. V. "Thiols as synthons." Russian Chemical Reviews 62, no. 8 (1993): 769–86. http://dx.doi.org/10.1070/rc1993v062n08abeh000046.

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9

Vidal-Albalat, A., K. Świderek, J. Izquierdo, S. Rodríguez, V. Moliner, and F. V. González. "Catalytic enantioselective epoxidation of nitroalkenes." Chemical Communications 52, no. 65 (2016): 10060–63. http://dx.doi.org/10.1039/c6cc03539f.

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10

Bharadwaj, Parimal K. "Metal ion binding by laterally non-symmetric macrobicyclic oxa–aza cryptands." Dalton Transactions 46, no. 18 (2017): 5742–75. http://dx.doi.org/10.1039/c7dt00722a.

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11

Wang, Xiaojuan, Minmin Kong, Duanxiu Li, Jianhui Fang, Zongwu Deng, and Hailu Zhang. "Stanozolol–aromatic carboxylic acid crystalline complexes: flexible tautomeric/ionization states and supramolecular synthons." CrystEngComm 21, no. 13 (2019): 2144–53. http://dx.doi.org/10.1039/c8ce01439f.

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12

Seth, Saikat Kumar, Vannajan Sanghiran Lee, Janchai Yana, et al. "Crystallographic and computational study of 1-(arylamino)-1,2,3-triazole-4-carbohydrazides." CrystEngComm 17, no. 11 (2015): 2255–66. http://dx.doi.org/10.1039/c4ce02175d.

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13

Tarai, Arup, and Jubaraj B. Baruah. "Oxime synthons in the salts and cocrystals of quinoline-4-carbaldoxime for non-covalent synthesis." CrystEngComm 18, no. 2 (2016): 298–308. http://dx.doi.org/10.1039/c5ce02029h.

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14

Felpin, François-Xavier, and Saumitra Sengupta. "Biaryl synthesis with arenediazonium salts: cross-coupling, CH-arylation and annulation reactions." Chemical Society Reviews 48, no. 4 (2019): 1150–93. http://dx.doi.org/10.1039/c8cs00453f.

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15

Yin, Wenqing, and Xuelian Wang. "Recent advances in iminyl radical-mediated catalytic cyclizations and ring-opening reactions." New Journal of Chemistry 43, no. 8 (2019): 3254–64. http://dx.doi.org/10.1039/c8nj06165c.

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16

Mehra, Vishu, Isha Lumb, Amit Anand, and Vipan Kumar. "Recent advances in synthetic facets of immensely reactive azetidines." RSC Adv. 7, no. 72 (2017): 45763–83. http://dx.doi.org/10.1039/c7ra08884a.

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17

Ni, Hao, Xiaoqian He, Kangbao Zhong, et al. "Oxymetalation or oxidative cyclization? mechanism of Pd-catalyzed annulation of enynones." Chemical Communications 57, no. 67 (2021): 8316–19. http://dx.doi.org/10.1039/d1cc02744a.

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18

Kumar, Yogesh, Prabhpreet Singh та Gaurav Bhargava. "Recent developments in the synthesis of condensed β-lactams". RSC Advances 6, № 101 (2016): 99220–50. http://dx.doi.org/10.1039/c6ra20973d.

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19

Frankowski, Sebastian, Justyna Kowalska, and Anna Albrecht. "Pyridylacetic acids and related systems as alkylheteroarene surrogates in asymmetric decarboxylative Michael addition." Chemical Communications 57, no. 27 (2021): 3387–90. http://dx.doi.org/10.1039/d0cc08182e.

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20

Fu, Junkai, Giuseppe Zanoni, Edward A. Anderson та Xihe Bi. "α-Substituted vinyl azides: an emerging functionalized alkene". Chemical Society Reviews 46, № 23 (2017): 7208–28. http://dx.doi.org/10.1039/c7cs00017k.

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21

Garg, Utsav, Yasser Azim, Aranya Kar, and Chullikkattil P. Pradeep. "Cocrystals/salt of 1-naphthaleneacetic acid and utilizing Hirshfeld surface calculations for acid–aminopyrimidine synthons." CrystEngComm 22, no. 17 (2020): 2978–89. http://dx.doi.org/10.1039/d0ce00106f.

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22

Roemer, Max, Brian W. Skelton, Matthew J. Piggott, and George A. Koutsantonis. "1,1′-Diacetyloctamethylferrocene: an overlooked and overdue synthon leading to the facile synthesis of an octamethylferrocenophane." Dalton Transactions 45, no. 47 (2016): 18817–21. http://dx.doi.org/10.1039/c6dt03820d.

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23

Xie, Jianing, Xuetong Li та Arjan W. Kleij. "Pd-catalyzed stereoselective tandem ring-opening amination/cyclization of vinyl γ-lactones: access to caprolactam diversity". Chemical Science 11, № 33 (2020): 8839–45. http://dx.doi.org/10.1039/d0sc03647a.

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24

Tran, Ngon T., Sean O. Wilson, and Annaliese K. Franz. "Supramolecular hydrogen-bonding assembly of silanediols with bifunctional heterocycles." Chem. Commun. 50, no. 28 (2014): 3738–40. http://dx.doi.org/10.1039/c4cc00672k.

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25

Mathiyazhagan, Arun Divakar, and Gopinathan Anilkumar. "Recent advances and applications of p-toluenesulfonylmethyl isocyanide (TosMIC)." Organic & Biomolecular Chemistry 17, no. 28 (2019): 6735–47. http://dx.doi.org/10.1039/c9ob00847k.

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26

Mukherjee, Arijit, Joan Teyssandier, Gunther Hennrich, Steven De Feyter, and Kunal S. Mali. "Two-dimensional crystal engineering using halogen and hydrogen bonds: towards structural landscapes." Chemical Science 8, no. 5 (2017): 3759–69. http://dx.doi.org/10.1039/c7sc00129k.

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27

Matamoros, Esther, Pedro Cintas, and Juan C. Palacios. "Amphipathic 1,3-oxazolidines from N-alkyl glucamines and benzaldehydes: stereochemical and mechanistic studies." New Journal of Chemistry 45, no. 9 (2021): 4365–86. http://dx.doi.org/10.1039/d0nj05503d.

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28

Zimmer, Reinhold, and Hans-Ulrich Reissig. "Alkoxyallenes as building blocks for organic synthesis." Chem. Soc. Rev. 43, no. 9 (2014): 2888–903. http://dx.doi.org/10.1039/c3cs60429b.

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29

Šterman, Andrej, Izidor Sosič, Stanislav Gobec, and Zdenko Časar. "Synthesis of aminoboronic acid derivatives: an update on recent advances." Organic Chemistry Frontiers 6, no. 16 (2019): 2991–98. http://dx.doi.org/10.1039/c9qo00626e.

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30

Smith, Merry K., and Ognjen Š. Miljanić. "Arylene ethynylene macrocycles: from molecular hosts to components of high-performance supramolecular architectures." Organic & Biomolecular Chemistry 13, no. 29 (2015): 7841–45. http://dx.doi.org/10.1039/c5ob01101a.

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31

Zhu, Ren-Yi, Long Chen, Xiao-Si Hu, Feng Zhou, and Jian Zhou. "Enantioselective synthesis of P-chiral tertiary phosphine oxides with an ethynyl group via Cu(i)-catalyzed azide–alkyne cycloaddition." Chemical Science 11, no. 1 (2020): 97–106. http://dx.doi.org/10.1039/c9sc04938j.

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32

Kaur, Gurpreet, and Angshuman Roy Choudhury. "A comprehensive understanding of the synthons involving C–H⋯F–C hydrogen bond(s) from structural and computational analyses." CrystEngComm 17, no. 15 (2015): 2949–63. http://dx.doi.org/10.1039/c5ce00215j.

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33

Bolla, Geetha, Sudhir Mittapalli, and Ashwini Nangia. "Modularity and three-dimensional isostructurality of novel synthons in sulfonamide–lactam cocrystals." IUCrJ 2, no. 4 (2015): 389–401. http://dx.doi.org/10.1107/s2052252515004960.

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The design of novel supramolecular synthons for functional groups relevant to drugs is an essential prerequisite for applying crystal engineering in the development of novel pharmaceutical cocrystals. It has been convincingly shown over the past decade that molecular level control and modulation can influence the physicochemical properties of drug cocrystals. Whereas considerable advances have been reported on the design of cocrystals for carboxylic acids and carboxamide functional groups, the sulfonamide group, which is a cornerstone of sulfa drugs, is relatively unexplored for reproducible h
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34

Král, Vladimír, Mikhail Ivanovich Kanishchev, Viktor Vladimirovich Semenov, Zdeněk Arnold, Svyatoslav Arkadievich Shevelev, and Albert Aleksandrovich Fainzilberg. "Synthetic utilization of N-diformylmethylazoles: The preparation of 1-heteryl-4-nitropyrazoles." Collection of Czechoslovak Chemical Communications 53, no. 7 (1988): 1529–33. http://dx.doi.org/10.1135/cccc19881529.

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35

Boyd, Derek R., Narain D. Sharma, John F. Malone, et al. "Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes." Organic & Biomolecular Chemistry 14, no. 9 (2016): 2651–64. http://dx.doi.org/10.1039/c5ob02411k.

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36

Wang, Mei-Xiang. "Exploring tertiary enamides as versatile synthons in organic synthesis." Chemical Communications 51, no. 28 (2015): 6039–49. http://dx.doi.org/10.1039/c4cc10327k.

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37

Brown-Xu, Samantha E., Malcolm H. Chisholm, Christopher B. Durr, Thomas F. Spilker, and Philip J. Young. "MM quadruply bonded complexes supported by vinylbenzoate ligands: synthesis, characterization, photophysical properties and application as synthons." Chemical Science 6, no. 3 (2015): 1780–91. http://dx.doi.org/10.1039/c4sc02542c.

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38

Zhong, Chen, Qi Yin, Yukun Zhao, Qinfeng Li, and Lin Hu. "Formal [5+1] annulation reactions of dielectrophilic peroxides: facile access to functionalized dihydropyrans." Chemical Communications 56, no. 86 (2020): 13189–92. http://dx.doi.org/10.1039/d0cc05565d.

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39

Han, Tian-Jiao, Min-Can Wang, and Guang-Jian Mei. "2-Indolymethanols as 4-atom-synthons in oxa-Michael reaction cascade: access to tetracyclic indoles." Chemical Communications 57, no. 71 (2021): 8921–24. http://dx.doi.org/10.1039/d1cc03653j.

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40

Surpateanu, Gheorghe, Ileana Denisa Nistor, Ana-Maria Georgescu, and Neculai Catalin Lungu. "Syntone Chemistry. Theoretical study on the formation of glycine, alannine and serine." Revista de Chimie 70, no. 5 (2019): 1707–11. http://dx.doi.org/10.37358/rc.19.5.7198.

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Three synthons: methylene, nitrene and carbon monoxide form aziridinone in the presence of molecular nitrogen at low temperatures. This one, in contact with the same three synthons could form the precursors of the first proteinogenic amino acids. This paper is a theoretical, thermodynamically and reactivity study concerning the formation of the three previously named amino acids at low temperature conditions. The key intermediates are identified in the formation of the three amino acids: aziridinone, aziridinonil and methyl-aziridinonil radicals. The quantitative results, enthalpies of formati
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41

Madhavi, N. N. L., Gautam R. Desiraju, Claire Bilton, Judith A. K. Howard, and Frank H. Allen. "Crystal engineering in the gem-alkynol family: interplay between strong and weak interactions in structures of 2,3,5,6-tetrahalo[F,Cl,Br]-trans-1,4-diethynylcyclohexa-2,5-diene-1,4-diols." Acta Crystallographica Section B Structural Science 56, no. 6 (2000): 1063–70. http://dx.doi.org/10.1107/s0108768100011496.

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Structures of the title compounds are all mediated by strong cooperative arrangements of O—H...O hydrogen bonds, supported by a variety of weaker interactions which affect the type of O—H...O synthon that is formed. The tetrafluoro compound contains hexameric O—H...O synthons in a supramolecular chair conformation, together with C≡C—H...F interactions. However, the tetrachloro and tetrabromo compounds both form tetrameric O—H...O synthons. This dominant pattern is supported by halogen...halogen interactions having one C—Cl[Br]...Cl[Br] angle close to 180° and the other close to 90°, and by C≡C
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42

Zhang, Wen-Hui, Yan-you Zhou, Xue-Wen He, Yi Gong, Xiong-Li Liu, and Ying Zhou. "An asymmetric iminium ion catalysis-enabled cascade cycloaddition reaction of chromone-oxindole synthons with enals: construction of a spirooxindole–hexahydroxanthone framework." Organic & Biomolecular Chemistry 17, no. 36 (2019): 8369–73. http://dx.doi.org/10.1039/c9ob01670h.

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43

Do, Nhan T., Khoa M. Tran, Hao T. Phan, Tuong A. To, Tung T. Nguyen, and Nam T. S. Phan. "Functionalization of activated methylene C–H bonds with nitroarenes and sulfur for the synthesis of thioamides." Organic & Biomolecular Chemistry 17, no. 40 (2019): 8987–91. http://dx.doi.org/10.1039/c9ob01751h.

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44

Ma, Xingxing, Shuilin Deng, and Qiuling Song. "Halodifluoroacetates as formylation reagents for various amines via unprecedented quadruple cleavage." Organic Chemistry Frontiers 5, no. 24 (2018): 3505–9. http://dx.doi.org/10.1039/c8qo00727f.

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45

Sánchez-Viveros, José Manuel, Job Bucio-Ortega, Naytzé Ortiz-Pastrana, and Juan Olguín. "Mononuclear complexes of FeII, CoII and CoIII containing imine-based ligands of 8-aminoquinoline and 7-aminoindazole: spin state tuning of FeII complexes in solution." New Journal of Chemistry 43, no. 25 (2019): 9776–83. http://dx.doi.org/10.1039/c9nj01622h.

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46

Xu, Junyu, Jing Cao, Chao Fang, Tao Lu, and Ding Du. "Organocatalytic C–C bond activation of cyclopropenones for ring-opening formal [3 + 2] cycloaddition with isatins." Organic Chemistry Frontiers 4, no. 4 (2017): 560–64. http://dx.doi.org/10.1039/c6qo00734a.

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47

Chinchilla, Rafael, and Carmen Nájera. "Acylvinyl and Vinylogous Synthons†." Chemical Reviews 100, no. 6 (2000): 1891–928. http://dx.doi.org/10.1021/cr9900174.

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48

Uneyama, Kenji, Toshimasa Katagiri та Hideki Amii. "α-Trifluoromethylated Carbanion Synthons". Accounts of Chemical Research 41, № 7 (2008): 817–29. http://dx.doi.org/10.1021/ar7002573.

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49

Luh, Tien-Yau, and Chin-Fa Lee. "Dithioacetals as Zwitterion Synthons." European Journal of Organic Chemistry 2005, no. 18 (2005): 3875–85. http://dx.doi.org/10.1002/ejoc.200500245.

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50

Kvasnička, V., and J. Pospíchal. "Graph theory of synthons." International Journal of Quantum Chemistry 38, no. 2 (1990): 253–78. http://dx.doi.org/10.1002/qua.560380222.

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