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Using AM-1 we have calculated the enthalpies of formation for 1-methyl-4-imidazole carboxamide, 1-methyl-4-pyrazole carboxamide, and 1-methyl-4-pyrrole carboxamide. These calculations give evidence that C-4 carbamoyl-1-alkyl imidazoles and pyrazoles may prefer an anti conformation in the gas phase by 5.5 and 2.9 kcal/mole, respectively. For 1-methyl-4-pyrrole carboxamide the two conformations differ by only 1.3 kcal/mol. Semi-empirical calculations were performed using Hyperchem release 2 on a Gateway 2000 PC utilizing a Intel 486 DX2-66 microprocessor. The geometries of the model compounds were optimized and their enthalpies of formation were calculated in vacuo with a Fletcher-Reeves (conjugate gradient) algorithm to a final RMS gradient of 0.01 kcal/Å mol.
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