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s-inf-n--inf-2-reaction
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Influence of a β-OH substituent on S<inf>Ninf>2 reactions of fluoroethane: Intramolecular hydrogen bonding catalysis or inhibition? A theoretical study
, Article Computational and Theoretical Chemistry ; Volume 1067 , 2015 , Pages 71-83 ; 2210271X (ISSN) ; Fattahi, A ; Sharif University of Technology
Abstract
Computational investigations on the gas phase SN 2 reactions of X ions (X-=OH-,F-,Cl-,Br-, and I-) with fluoroethane and 2-fluoroethanol (β-hydroxyl ethyl fluoride) were performed by using MPW1K, M06 and CCSD(T) methods with a range of basis sets including 66-311++G**, TZVP, aug-cc-pVDZ and SDD. To better understand the nature of the corresponding intermolecular interactions, we performed natural bond orbital (NBO) analysis and Bader's quantum theory of atoms in molecules (QTAIM). In our calculations, we took into account two possible pathways for these reactions, i.e. SN 2 reactions of 2-fluoroethanol. In path(i), β-hydroxyl group participates in hydrogen bonding...