Proton Transfer Tautomerization inN-Salicylideneanilines upon Charge-Transfer Complex Formation. 7,7,8,8-Tetracyanoquinodimethane (TCNQ) and 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ) Complexes ofN-(2-Hydroxy-1-naphthylmethylene)-1-pyrenamine andN,N′-Bis(2-hydroxy-1-naphthylmethylene)-p-phenylenediamine

Autor:	Yusei Maruyama, Tadaoki Mitani, Isabelle Luneau, Naomi Hoshino-Miyajima, Tamotsu Inabe
Rok vydání:	1994
Předmět:	chemistry.chemical_compound Crystallography Nitrile Chemistry Hydrogen bond Stereochemistry Intramolecular force Molecule General Chemistry Crystal structure Charge-transfer complex Tautomer Tetracyanoquinodimethane
Zdroj:	Bulletin of the Chemical Society of Japan. 67:622-632
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.67.622
Popis:	TCNQ and F4TCNQ complexes of N-(2-hydroxy-1-naphthylmethylene)aniline-type compounds, N-(2-hydroxy-1-naphthylmethylene)-1-pyrenamine (NPY) and N,N′-bis(2-hydroxy-1-naphthylmethylene)-p-phenylenediamine (DNP) have been prepared and subjected to structural and optical studies in the crystalline state. An X-ray crystallographic study indicates that the donors and acceptors are mixed along a one-dimensional column in all complexes. The intramolecular O–H···N hydrogen bond structure is sensitively changed upon complex formation; the hydrogen atom is located at the nitrogen site in TCNQ complexes and shifts to the center of the hydrogen bond in F4TCNQ complexes. The hydrogen-bond structure is found to vary with some correlation to the strength of the charge-transfer interaction.
Databáze:	OpenAIRE
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