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- W955268035 abstract "The molecular and electronic structure of 2-methyl, 2-amino-histamine derivatives, and 5-(2′-aminoethyl)-2,4-dimethylthiazole heve been studied by means of ab initio quantum mechanical calculations at 6-31G**//6-31G** and MP2/6-31G**//6-31G** levels. Tautomers and conformers (T/C) of these derivatives were characterized as neutral and monocation forms. Most stable T/C’s of these compounds have the alkyl chain oriented towards the heterocyclic ring in a gauche disposition with an electrostatic internal interaction. Topology of the electronic charge density has been performed in the main structures in order to characterize internal hydrogen bonds and interactions. Proton affinity (PA) differences relative to ammonia of these compounds have been calculated by using direct and isodesmic reactions. This study of PA has been extended at the MP2/6-31G**//6-31G** level for histamine (4(5)-2′-aminoethylimidazole), 4-methyl, 4-chloro, 4-nitro, Nα-methyl, and Nα,Nα-dimethyl-histamine derivatives, amthamine (2-amino-5-(2′-aminoethyl)-4-methylthiazol) and amthamine derivatives (2-amino-5-(2′-aminoethyl)-thiazole, and 4-methyl-5-(2′-aminoethyl)-thiazole). All histamine derivatives are strong bases in the gas phase, especially the Nα,Nα-dimethyl) derivative. Amthamine yields conformers and PA very close to that of the histamine. The calculated PA values at the three levels (MP2/6-31G**//6-31G**, 6-31G**//6-31G** and MP2/6-31G**//MP2/6-31G** (only for the leader compounds)) show similar values.PA values of the gauche tautomers correlate with the proton association constants of the nitrogens of imidazolyl or thiazolyl groups of these compounds and also with the receptor bindings at H2 receptors of histamine. Relationships between molecular structure and its possible interaction with the H2 receptor are discussed.KeywordsPotential Energy SurfaceProton AffinityImidazole RingBond Critical PointThiazole RingThese keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves." @default.
- W955268035 created "2016-06-24" @default.
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- W955268035 date "2005-12-30" @default.
- W955268035 modified "2023-10-11" @default.
- W955268035 title "Theoretical Study of the Proton Affinities of Some Substituted Derivatives of Histamine and Homologous Compounds. Structure-Activity Relationships" @default.
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- W955268035 doi "https://doi.org/10.1007/0-306-48145-6_20" @default.
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