Show simple item record Kraszni, Marta Kokosi, Jozsef Noszal, Bela 2023-05-26T10:01:20Z 2023-05-26T10:01:20Z 2002
dc.identifier 0036014017
dc.identifier.citation journalIssueNumber=5;journalTitle=JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2;pagerange=914-917;journalAbbreviatedTitle=J CHEM SOC PERKIN TRANS 2;
dc.identifier.uri doi:
dc.description.abstract A method was developed and applied to determine the populations and site- and conformer-specific basicities of histamine rotamers in three distinct states of protonation. The method that has been developed also allows the determination of molecule- and position-specific standard gauche and trans H-1 NMR coupling constants, and the subsequent rotamer analysis from NMR spin systems with a single observed coupling constant, introducing simplifying allowances of symmetry origin. Synthesis and NMR analysis of a reference histamine derivative have also been carried out. The trans rotamers of histamine were found to exist in 41, 38 and 50% in the neutral, monocationic and dicationic forms, respectively, providing quantitative, experimental evidence for the preferential thermodynamic properties of the trans species over the two enantiomeric, statistically favoured g conformers in any ionisation form. Quanti cation of the rotamer- and site- specific basicities resulted in increased amino and decreased imidazole basicities in the gauche rotamer, indicating the formation of intramolecular hydrogen bonds in the monocationic form.
dc.format.extent 914-917
dc.title Concentration and basicity of histamine rotamers
dc.type Journal Article 2023-05-11T13:43:26Z
dc.language.rfc3066 en
dc.rights.holder NULL
dc.identifier.mtmt 1478240
dc.identifier.wos 000175325400010
dc.contributor.department SE/GYTK/Gyógyszerészi Kémiai Intézet
dc.contributor.institution Semmelweis Egyetem

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