Tautomerism in the Solid State and in Solution of a Series of 6-Aminofulvene-1-aldimines.

DIONISIA SANZ; MARTA PEREZ TORRALBA; SERGIO ALARCON; ROSA CLARAMUNT; CONCEPCIÓN FOCES-FOCES; JOSÉ ELGUERO

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 2002 vol. 67 p. 1462 - 1471

0022-3263

To study systems able to sustain intramolecular proton-transfer, we have prepared a series of sixaminofulvene aldimines including several labeled with 15N and 2H. These compounds show couplingconstants through the hydrogen bond, 1hJ(15N-1H) and 2hJ(15N-15N). The position of the tautomeric equilibria, i.e., on what nitrogen atom is the proton, was determined in the solid state and in solution. The crystal structure of N{[5-[(phenylamino)methylene]-1,3-cyclopentadien-1-yl]methylene}pyrrole-1-amine (3) has been determined by X-ray analysis. In solution, both N-H and C-H tautomers were observed and their structures assigned by NMR spectroscopy. Particularly useful is the value of the 1J(15N-1H) coupling constant.