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Gas‐phase Diels–Alder cycloaddition reaction in the presence of methanol and water vapor
Author(s) -
Gholami M. R.,
Talebi B. A.
Publication year - 2003
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.577
Subject(s) - chemistry , methanol , cycloaddition , hydrogen bond , hydrogen , photochemistry , ab initio , computational chemistry , organic chemistry , catalysis , molecule
Hydrogen bonding effects of protic solvents, apart from bulk properties, on the reaction rate of the cycloaddition of cylopentadiene and vinyl acetate in the presence of water and methanol in the gas phase were investigated. The results showed that methanol increases the reaction rate in the gas phase more than the water. This is attributed to the stronger hydrogen bonding effect of methanol in this phase. Ab initio and semi‐empirical calculations show that methanol stabilizes the transition state of the reaction more than water. This arises from two different origins, distribution of charge and geometry of the hydrogen bond. Copyright © 2002 John Wiley & Sons, Ltd.