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Structure of N-chloromethyllactams and features of the interaction of atoms in them as a result of ab initio calculations

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Chemistry of Heterocyclic Compounds Aims and scope

Quantum-chemical calculations have been carried out by the RHF/6-31G(d) and MP2/6-31+G(d) methods of molecules of N-chloromethylpyrrolidone, N-chloromethylcaprolactam, N-chloromethyl-succinimide, and N-chloromethylphthalimide with full optimization of their geometry, and also N-chloromethylpyrrolidone molecule by the RHF/6-31G(d) method at various angles of rotation of the CH2Cl group around the C―N bond. It was shown that the lower frequencies of the 35Cl NQR of the first two molecules in comparison with the later are mainly determined by the high populations of the p σ -orbitals of their Cl atoms. The population of the orbitals of the unshared electron pair of the N atom is practically unchanged on rotating the CH2Cl group, but the N atom polarizes the C―Cl bond in the indicated molecule. This does not confirm the supposed p,σ*-conjugation in the Cl―C―N grouping.

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Authors and Affiliations

  1. Institute of Technical Chemistry, Ural Branch of the Russian Academy of Sciences, Perm, 614013, Russia

    V. P. Feshin & E. V. Feshina

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  1. V. P. Feshin
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  2. E. V. Feshina
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Correspondence to V. P. Feshin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1537–1544, October, 2008.

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Feshin, V.P., Feshina, E.V. Structure of N-chloromethyllactams and features of the interaction of atoms in them as a result of ab initio calculations. Chem Heterocycl Comp 44, 1250–1256 (2008). https://doi.org/10.1007/s10593-009-0170-5

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