Premium
The stepwise heats of hydrogenation of barrelene, an ab initio study
Author(s) -
Schmitz Lawrence R.,
Allinger Norman L.,
Flurchick Kenneth M.
Publication year - 1988
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.540090402
Subject(s) - bicyclic molecule , ab initio , octane , standard enthalpy of formation , chemistry , computational chemistry , double bond , octene , ab initio quantum chemistry methods , thermodynamics , physics , stereochemistry , catalysis , organic chemistry , molecule , ethylene
Ab initio Hartree‐Fock calculations at the 6–31G*//3–21G level of theory are reported for bicyclo[2.2.2]‐2,5,7‐octatriene (barrelene), 1 , bicyclo[2.2.2]‐2,5‐octadiene, 2 , bicyclo[2.2.2]‐2‐octene, 3 , and bicyclo‐[2.2.2]octane, 4 . The stepwise heats of hydrogenation of 1 were found to be 38.1, 31.8, and 28.4 kcal/mol, respectively. The unusually large heat of hydrogenation for the first double bond is attributed to the destabilizing electronic effects involving the interaction of the three double bonds of 1 .
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom