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Selection of Betaine Building Blocks for the Construction of Quadrupolar Heterophane Frameworks
Author(s) -
PérezGarcía Lluïsa,
Mesquida Neus,
Alemany Montserrat,
Fernández Irene,
Vilaseca Marta,
Alcalde Ermitas
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200208)2002:16<2691::aid-ejoc2691>3.0.co;2-t
Subject(s) - chemistry , betaine , electrospray ionization , benzimidazole , non covalent interactions , dipole , mass spectrometry , chemical polarity , electrospray , computational chemistry , electrospray mass spectrometry , pyrazole , stereochemistry , crystallography , molecule , hydrogen bond , organic chemistry , chromatography
The synthesis of a set of [(azolio)methyl]azolate betaines 3 − 6 designed by combination of a variety of heterocyclic fragments based on pyrazole, 1,2,4‐triazole, and benzimidazole is reported. The dipolar nature of the betaines is discussed on the basis of 1 H and 13 C NMR spectroscopic data and dipole moment values, which range between 13.4 and 16.5 D. By exploitation of the sensitivity of electrospray ionization mass spectrometry in both the positive and negative modes, several informative peaks and stable noncovalent polymolecular self‐assembled structures in the gas phase were observed. From these results, the [(imidazolio)methyl]‐1,2,4‐triazolate betaine subunits 1 were chosen as the most suitable building blocks for the construction of quadrupolar [1 n ]heterophanes. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)