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3224647 
Journal Article 
Quantum Mechanical Study on Hydrogen Bonds between 3-Aminophenol and CHxCl4-x (x=1, 2, 3): Effect of the Number of Halogen Atoms 
Lee, SoY; Kang, H 
2015 
Yes 
Bulletin of the Korean Chemical Society
ISSN: 0253-2964
EISSN: 1229-5949 
36 
3 
752-756 
WOS:000353574800008 
Hydrogen bonds between 3-aminophenol and three chlorine-substituted methanes (CHCl3, CH2Cl2, and CH3Cl) 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 C-H stretching vibrations were investigated. When it is hydrogen-bonded to 3-aminophenol (3AP), the CH stretching frequency of CHCl3 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 C-H stretches of CH2Cl2 and CH3Cl 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 pi-hydrogen bond to 3AP but only CHCl3, the one with the most chlorine atoms, makes a blue-shifting hydrogen bond, or an "antihydrogen bond". 
Antihydrogen bond; blue-shifting hydrogen bond; 3-Aminophenol; Halomethane