Steric effects in hydrogen bonded columns of salts of benzoic acid and 1-adamantanecarboxylic acid with the cyclic amines CnH2n+1NH2, n = 5, 6, 7, 8 and 12
作者： Andreas Lemmerer
DOI: 10.1039/C0CE00749H
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摘要: The hydrogen bonded columns of salts benzoic acid or adamantanecarboxylic and five cyclic amines are reported. During solution crystallization, the H from carboxylic transfers to amine form ammonium carboxylate which feature three charge-separated N+–H⋯O−hydrogen bonds two types 1-D columns. Of ten structures, viz. (cyclopentylammonium·benzoate) (1), (cyclohexylammonium·benzoate) (2), (cyclododecylammonium·benzoate) (5), (cyclopentylammonium·adamantanecarboxylate) (6), (cyclohexylammonium·adamantanecarboxylate) (7) (cyclododecylammonium·adamantanecarboxylate) (10) a type IIhydrogen column consists repeating R34(10) rings whereas (cycloheptylammonium·benzoate) (3), (cyclooctylammonium·benzoate) (4), (cycloheptylammonium·adamantanecarboxylate) (8), (cyclooctylammonium·adamantanecarboxylate) (9) IIIhydrogen column, alternating R24(8)/R44(12) rings. Even with sterically different anions, formed is same for each counter cation hence it size that influences column. From this we can gather clues about effect steric anion its on overall packing.
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sci-hub.se 参考文章(45)
Akira Tanaka, Ichiro Hisaki, Norimitsu Tohnai, Mikiji Miyata, Supramolecular Tilt Chirality Derived from Symmetrical Benzene Molecules: Handedness of the 21 Helical Assembly Chemistry-an Asian Journal. ,vol. 2, pp. 230- 238 ,(2007) , 10.1002/ASIA.200600332
Frank H. Allen, Olga Kennard, David G. Watson, Lee Brammer, A. Guy Orpen, Robin Taylor, Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds Journal of The Chemical Society-perkin Transactions 1. ,(1987) , 10.1039/P298700000S1
Miguel A. Mateos-Timoneda, Mercedes Crego-Calama, David N. Reinhoudt, Supramolecular chirality of self-assembled systems in solution Chemical Society Reviews. ,vol. 33, pp. 363- 372 ,(2004) , 10.1039/B305550G
Biserka Kojic-Prodic, Kresimir Molcanov, The Nature of Hydrogen Bond : New Iinsights Into Old Theories Acta Chimica Slovenica. ,vol. 55, pp. 692- 708 ,(2008)
C. V. Krishnamohan Sharma, Crystal Engineering−Where Do We Go from Here? Crystal Growth & Design. ,vol. 2, pp. 465- 474 ,(2002) , 10.1021/CG0200356
M. C. Etter, J. C. MacDonald, J. Bernstein, Graph-set analysis of hydrogen-bond patterns in organic crystals Acta Crystallographica Section B-structural Science. ,vol. 46, pp. 256- 262 ,(1990) , 10.1107/S0108768189012929
Christer B. Aakeröy, Kenneth R. Seddon, The hydrogen bond and crystal engineering Chem. Soc. Rev.. ,vol. 22, pp. 397- 407 ,(1993) , 10.1039/CS9932200397
Tetsuharu Yuge, Norimitsu Tohnai, Takeyoshi Fukuda, Ichiro Hisaki, Mikiji Miyata, Topological study of pseudo-cubic hydrogen-bond networks in a binary system composed of primary ammonium carboxylates : An analogue of an ice cube Chemistry: A European Journal. ,vol. 13, pp. 4163- 4168 ,(2007) , 10.1002/CHEM.200700099
Venu R. Vangala, Balakrishna R. Bhogala, Archan Dey, Gautam R. Desiraju, Charlotte K. Broder, Philip S. Smith, Raju Mondal, Judith A. K. Howard, Chick C. Wilson, Correspondence between molecular functionality and crystal structures. Supramolecular chemistry of a family of homologated aminophenols. Journal of the American Chemical Society. ,vol. 125, pp. 14495- 14509 ,(2003) , 10.1021/JA037227P
Margaret C. Etter, Encoding and decoding hydrogen-bond patterns of organic compounds Accounts of Chemical Research. ,vol. 23, pp. 120- 126 ,(1990) , 10.1021/AR00172A005