Abstract
Quantum chemical calculations of geometrical, electronic, and energy characteristics for aliphatic amines, ammonia, some α-amino acids, and 4-nitrophenyl benzoate (4-NPB) have been performed. By the QSPR method, it was found that the rate constants for the reactions of amino compounds specified with 4-NPB in water—propan-2-ol solvent mixture are linearly dependent on the contribution of the 2pz-AO of nitrogen into the HOMO, as well as on the population of the 2pz-AO of nitrogen. Different character of the dependencies for 6h-amino acids and aliphatic amines can be explained by their involvement into formation of solvato-complexes with different reactivity.
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References
A. P. Mikhalkin, Usp. Khim., 1995, 64, 275 [Russ. Chem. Rev. (Engl. Transl.), 1995, 64].
A. Al’bert, Izbiratel’naya toksichnost’. Fiziko-khimicheskie osnovy terapii [Selective Toxicity. Physico-chemical Bases of Therapy], Meditsina, Moscow, 1982, V. 2, p. 52 (in Russian).
A. A. Gershkovich, V. K. Kibirev, Khimicheskii sintez peptidov [Chemical Synthesis of Peptides], Naukova Dumka, Kiev, 1992, 488 pp. (in Russian).
L. V. Kuritsyn, T. P. Kustova, A. I. Sadovnikov, N. V. Kalinina, M. V. Klyuev, Ed. L. V. Kuritsyn, Kinetika reaktsii atsil’nogo perenosa [Kinetics of the Acyl Transfer Reactions], Ivanovo State Univ., Ivanovo, 2006, 260 pp. (in Russian).
L. N. Khripkova, L. V. Kuritsyn, N. V. Kalinina, Zh. Obshch. Khim., 2004, 74, 1665 [Russ. J. Gen. Chem. (Engl. Transl.), 2004, 74].
HyperChem™ Release 7.52 for Windows. Molecular Modeling System, Seriennr. 12-750-1503700446, Gainesville, Hypercube Inc., 2005.
L. M. Litvinenko, N. M. Oleinik, Mekhanizmy deistviya organicheskikh katalizatorov. Osnovnyi i nukleofil’nyi kataliz [Mechanisms of Action of Organic Catalysts. Base and Nucleophilic Catalysis], Naukova Dumka, Kiev, 1984, 264 pp. (in Russian).
V. F. Traven’, Elektronnaya struktura i svoistva organicheskikh molekul [Electronic Structure and Properties of Organic Molecules], Khimiya, Moscow, 1989, 384 pp. (in Russian).
L. M. Pritykin, O. B. Selyutin, Zh. Org. Khim., 1998, 34, 1197 [Russ. J. Org. Chem. (Engl. Transl.), 1998, 34]. Received June 14, 2007; in revised form April 9, 2008
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 725-729, April, 2009.
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Kochetova, L.B., Kalinina, N.V. & Kustova, T.P. Quantum chemical interpretation of reactivities of aliphatic amines and α-amino acids in acylation. Russ Chem Bull 58, 741–745 (2009). https://doi.org/10.1007/s11172-009-0088-1
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DOI: https://doi.org/10.1007/s11172-009-0088-1