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Electrostatic potential around halogenated anesthetics. Acidic hydrogen; chlorine vs. fluorine
Author(s) -
Ruelle P.,
Sandorfy C.
Publication year - 1982
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.560220404
Subject(s) - chemistry , fluorine , chlorine , chloroform , lone pair , hydrogen , chlorine atom , hydrogen bond , ab initio , computational chemistry , hydrogen atom , halogen , acceptor , ab initio quantum chemistry methods , binding energy , inorganic chemistry , molecule , medicinal chemistry , organic chemistry , atomic physics , group (periodic table) , alkyl , physics , condensed matter physics
Maps of electrostatic potential around a number of halocarbon anethetics have been obtained through Gaussian ab initio calculations. Information is obtained on the mode of association of these compounds with possible receptors. The positive potential found along the extension of the CH bonds substantiates the role of the “acidic hydrogen.” The presence of fluorines on the carbon atom to which it is bound restricts the access to this positive site through the repulsive action of the fluorine lone pairs, an observation that explains the very different behavior of chloroform and fluoroform, for example, with respect to their anesthetic potencies and hydrogen bonding abilities. In the absence of an acidic hydrogen the chlorine atoms can serve as associative sites.