Structural studies on 9‐hydrazono‐6,7,8,9‐tetrahydro‐4‐oxo‐4 H ‐pyrido[1,2‐ a ]pyrimidines by  1 H,  13 C and  15 N NMR spectroscopy | Zendy

Tóth Gábor | Zendy; Szöllösy ÁRon | Zendy; Almásy Attila | Zendy; Podányi Benjámin | Zendy; Hermecz István | Zendy; Breining Tibor | Zendy; Mészáros Zoltán | Zendy

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Structural studies on 9‐hydrazono‐6,7,8,9‐tetrahydro‐4‐oxo‐4 H ‐pyrido[1,2‐ a ]pyrimidines by 1 H, 13 C and 15 N NMR spectroscopy

Author(s) -

Tóth Gábor,

Szöllösy ÁRon,

Almásy Attila,

Podányi Benjámin,

Hermecz István,

Breining Tibor,

Mészáros Zoltán

Publication year - 1983

Publication title -

organic magnetic resonance

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.483

H-Index - 72

eISSN - 1097-458X

pISSN - 0030-4921

DOI - 10.1002/omr.1270211111

Subject(s) - tautomer , steric effects , chemistry , substituent , hydrogen bond , solvation , carbon 13 nmr , nuclear magnetic resonance spectroscopy , proton , computational chemistry , stereochemistry , solvent , crystallography , molecule , organic chemistry , physics , quantum mechanics

1 H, 13 C and 15 N NMR studies demonstrated that 9‐hydrazono‐6,7,8,9‐tetrahydro‐4‐oxo‐4 H ‐pyrido‐[1,2‐ a ] pyrimidlnes exist as an equilibrium mixture of Z ‐ E isomers in the hydrazono–imino tautomeric form having an exocyclic double bond. Proton‐catalysed Z ‐ E interconversion is fast. Substituent and solvent effects revealed that the decisive factors controlling the Z:E ratio are internal hydrogen bonding in the Z ‐isomer, stabilization by solvation and steric interaction.

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