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Self‐assembly of molecules containing the 2‐aminopyridine unit in non‐polar solvents
Author(s) -
Rospenk Maria,
Koll Aleksander
Publication year - 2005
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.929
Subject(s) - chemistry , molecule , dipole , monomer , chemical polarity , hydrogen bond , pyridine , crystallography , polar , ring (chemistry) , self assembly , computational chemistry , organic chemistry , polymer , physics , astronomy
A combined experimental and theoretical study on the self‐assembly of three molecules, 2,2′‐dipyridylamine, 2‐(1‐phenylamino)pyridine and 2‐methylaminopyridine was performed. The effect of concentration increase in low‐polarity solvents was investigated. The average molecular weights, dipole moments and IR spectra of these compounds were measured in C 6 H 6 , CCl 4 and CHCl 3 . A strong association of all these molecules was found, through NH···N hydrogen bonding. The form of associates is different; in molecules containing the N ‐aromatic ring the aggregates have a dipole moment decreasing with concentration whereas in N ‐methylaminopyridine a considerable increase in dipole moment with concentration was observed. DFT B3LYP/6–31G(d,p) calculations for monomers, dimers, trimers and tetramers of these three molecules were performed to model the structures of possible aggregates. Copyright © 2005 John Wiley & Sons, Ltd.