4-tert-Butyl-1-aza-2-cyclohexanone

The thermodynamic properties of hydrogen bonding among lactams with ring sizes n \ 4, 5 and 6 were investigated using infrared spectroscopy of the fundamental NÈH stretching frequencies of both the monomer and dimer species. The results are consistent with a predominantly monomerÈdimer equilibrium with the dimer having symmetry. The thermodynamic properties (in for the four-, Ðve-and six-membered C 2 CCl 4 ) lactam rings are (at 25 ¡C) \ 12.4(9), 24(6) and 25(3), (kJ mol~1) \ [30(2), [30(1) and [28(2) and K d *H d (J mol~1 K~1) \ [79(4), [74( 3) and [67(5), respectively (precisions in parentheses). The experimentally *S d determined thermodynamic properties are compared with ab initio calculations (6È31G** basis set) which represent gas-phase results. The comparison of these two approaches yields a picture which is consistent with the notion that the primary e †ect of ring size is an entropy of solvation e †ect and not the enthalpy of hydrogen bonding between the monomer units.

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4-tert-Butyl-1-aza-2-cyclohexanone

Abstract: Abstract.C9HI7NO

Cited by 3 publications

References 6 publications

Organic Section

Organic Section

An ab initio quantum chemical study of reactions of hexano-6-lactam peroxy radicals with phenoxy or diphenyl radicals

Effects of lactam ring size on the thermodynamics of hydrogen bonding in CCl4 solutions: experimental and ab initio studies

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