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Chiral discrimination in hydrogen‐bonded complexes of butan‐2‐ol (m‐form) and hydrogen peroxide
Author(s) -
Yin Aixia,
Zhang Guiqiu,
Chen Dezhan
Publication year - 2009
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.21974
Subject(s) - chemistry , intermolecular force , hydrogen peroxide , hydrogen bond , hydrogen , crystallography , selectivity , stereochemistry , medicinal chemistry , computational chemistry , molecule , organic chemistry , catalysis
A theoretical study was reported on the chiral discrimination of different chiral formers of hydrogen‐bonded complexes of butan‐2‐ol (m‐form of “ga,” “ag,” and “gg”) with hydrogen peroxide. This completes, together with previous results on the butan‐2‐ol (h‐form)···HOOH complexes [Zhang et al., J Mol Struct (Theochem), 2008, 864, 56], the study of two forms of butan‐2‐ol: m‐form and h‐form. Altogether, 12 minimum structures were located, and they are bound by intermolecular hydrogen bonds. The largest chirodiastaltic energy of the two most stable complexes was found for (SM‐2)‐(SP‐2) of “gg”, at −0.238 kcal mol −1 in favor of the SM‐2 complex in the “gg” configuration. The largest diastereofacial energy was found for (SP‐2)‐SP of “ga,” at −3.763 kcal mol −1 in favor of the SP‐2 complex in the “ga” configuration. Moreover, the diastereofacial interactions lead to a preference for the SM‐2 and SP‐2 over the SM and SP for all the butan‐2‐ol (m‐form)···HOOH complexes. The values of the largest chirodiastaltic energy and diastereofacial energy are similar to butan‐2‐ol (h‐form), but the sign of the value (diastereofacial energy) is reverse. © 2009 Wiley Periodicals, Inc. Int J Quantum Chem, 2009