Tautomerism of bis(2,4-benzyloxy)-6-(5 H )-one-1,3,5-triazine: A combined crystallographic and quantum-chemical investigation
ABSTRACT In order to study the keto and enol forms of cyanuric acid derivatives in the solid state, we have synthesized bis(2,4-benzyloxy)-6-(5H)-one-1,3,5-triazine, 1. Computational investigations indicate that keto form is more stable than enol form in both gas phase and solution phase
by 9.69–11.18 kcal mol−1 IR and crystallographic analysis shows that 1 exists in keto form in the solid state also. To obtain the enol form in the solid state, we adopted co-crystallization with
an organic base. The crystal structures of both keto/amine and the enol/imine forms (in a co-crystal) are reported.
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ABSTRACT: In the crystal of triclinic symmetry the title compound contains four independent molecules, which differ in the conformation of the aliphatic carbon chain (T, G +and G −) and in the helicity (M or P) of the N-(1,8-naphthaloyl)-2-aminobenzoate (NAB) unit. Quantum chemical MP2 calculations showed that isolated molecules favor helicity of NAB bichromophores most likely due to attractive interactions between local dipoles formed along carbonyl bonds, such that the helical arrangement of O=C–C–C–N–C=O fragments is stabilized by intramolecular interactions between terminal anti-parallel local carbonyl dipoles. In the crystal structure, columnar stacking of the anti-parallel 1,8-naphalimide rings is observed. In a column the neighboring NAB units display opposite helicity.Structural Chemistry 07/2007; 18(3):379-386. DOI:10.1007/s11224-007-9182-x · 1.90 Impact Factor
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ABSTRACT: AbstractIn the current study we relate the contents of the journal of “Structural Chemistry” for the calendar year 2006 to thermochemistry. Each paper is briefly summarized and supplemented by a comment which explicitly interrelates the content of the study to chemical energetics.Structural Chemistry 12/2009; 20(6):1019-1037. DOI:10.1007/s11224-009-9506-0 · 1.90 Impact Factor