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Solvent effect on polar and spectroscopic properties of 2-N-methylamino-5-nitro-6-methylpyridine and 2-N-methylamino-3-nitro-6-methylpyridine

✍ Scribed by Zbigniew Pawełka; Barbara Palasek; Aniela Puszko

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
119 KB
Volume
10
Category
Article
ISSN
0894-3230

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✦ Synopsis

Dipole moments of 2-N-methylamino-5-nitro-6-methylpyridine (I) and 2-N-methylamino-3-nitro-6-methylpyridine (II) were determined in solvents of different polarity and basicity. The solvent effect is discussed in terms of the twoparameter (*-␤) Kamlet-Taft expression. The solvent dependences of the energy of intramolecular charge-transfer transition and the frequency of the (NH) stretching vibration are in keeping with the dielectric results. It was found that the solvent-induced disturbance in the electronic structure of I is brought about by hydrogen bond interaction with the NH group. The strong intramolecular hydrogen bond in II is stable in weakly basic solvents and the electronic structure is insensitive to the environment. However, in more basic solvents the intramolecular hydrogen bond is partly broken and an N-H• • •solvent hydrogen bond is formed, bringing about distinct changes in polarity and spectroscopic properties.

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