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INTRINSIC (GAS‐PHASE) BASICITIES AND STABILITY OFCHARGE‐TRANSFER COMPLEXES IN SOLUTION
Author(s) -
Bouab W.,
Esseffar M.,
Abboud J.L. M.
Publication year - 1997
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/(sici)1099-1395(199705)10:5<343::aid-poc892>3.0.co;2-b
Subject(s) - chemistry , ethylamine , dichloromethane , gibbs free energy , reactivity (psychology) , iodine , gas phase , phase (matter) , thermodynamics , computational chemistry , organic chemistry , medicine , physics , alternative medicine , pathology , solvent
The standard Gibbs energy changes for the formation of 1:1 charge‐transfer complexes between molecular iodine and several bases in solution at 25·0 °C [Δ G 0 l2 (soln)] were determined experimentally. The bases were 2,2,2‐trifluoro‐ ethylamine, cyclopropylamine and 1,1,3,3‐tetramethylguanidine. These [Δ G 0 l2 (soln)] values, determined in n ‐heptane, and also that for the formation of the 1:1 complex between 2,2,2‐trifluoroethanethiol and molecular iodine in dichloromethane, were found to follow with excellent precision the correlation equations linking Δ G 0 l2 (soln) and the intrinsic (gas‐phase) basicities of N(sp 3 ), N(sp 2 ) and S(sp 3 ) bases. These findings strongly support previous conclusions regarding the relationship between gas‐phase and solution reactivity data. © 1997 John Wiley & Sons, Ltd.