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Theoretical studies on the intramolecular cyclization of alkyl halide anions
Author(s) -
Lee Ikchoon,
Kim Chang Kon
Publication year - 1990
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.540111002
Subject(s) - chemistry , halide , reactivity (psychology) , fluoride , intramolecular force , chloride , medicinal chemistry , ring (chemistry) , alkyl , enthalpy , ion , inorganic chemistry , organic chemistry , medicine , physics , alternative medicine , pathology , quantum mechanics
The intramolecular cyclization reactions of alkyl fluoride and chloride anions 1 were investigated theoretically using the AM1 method. Formation of five‐membered ring was the most reactive and that of three‐membered ring was the least reactive process in both series. For the fluoride series the reactivity order of n = 5 > 6 > 7 > 4 > 3 was dictated by the enthalpy (ΔH≠) effect while for the chloride series the entropy (ΔS≠) effect was found to play somewhat greater role due to the much better leaving ability of the chloride anion leading to the reactivity order of n = 5 > 6 > 4 > 7 > 3. For both series, BEP principle held and the degree of bond formation was greater with the fluoride series owing to the poor electron acceptor ability of the cleaving bond.