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Quantum Mechanical Study on Hydrogen Bonds between 3‐Aminophenol and CH x Cl 4 − x ( x = 1, 2, 3): Effect of the Number of Halogen Atoms #
Author(s) -
Lee So Young,
Kang Hyuk
Publication year - 2015
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.10137
Subject(s) - chemistry , hydrogen bond , hydrogen , chlorine , photochemistry , bond energy , triple bond , crystallography , molecule , double bond , organic chemistry
Hydrogen bonds between 3‐aminophenol and three chlorine‐substituted methanes ( CHCl 3 , CH 2 Cl 2 , and CH 3 Cl ) were quantum mechanically studied at MP2 /aug‐cc‐ pVDZ level. Several low‐energy structures with a hydrogen bond were identified for all chlorinated methanes, and the properties of their CH stretching vibrations were investigated. When it is hydrogen‐bonded to 3‐aminophenol (3AP), the CH stretching frequency of CHCl 3 is blue‐shifted by 18–54 cm −1 , and its IR absorption intensity is 48–74 times increased, depending on the isomer. The symmetric and antisymmetric CH stretches of CH 2 Cl 2 and CH 3 Cl are shifted in either direction by a few cm −1 upon hydrogen‐bonding to 3AP, and their IR intensity was increased by a few times. It is concluded that all chlorinated methanes can make a π‐hydrogen bond to 3AP but only CHCl 3 , the one with the most chlorine atoms, makes a blue‐shifting hydrogen bond, or an “antihydrogen bond”.