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Influence of Deuteration and Fluorination on the Supramolecular Architecture of Pyridine N‐Oxide Crystals
Author(s) -
Shishkin Oleg V.,
Shishkina Svitlana V.,
Maleev Andrey V.,
Zubatyuk Roman I.,
Vasylyeva Vera,
Merz Klaus
Publication year - 2013
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201200581
Subject(s) - supramolecular chemistry , pyridine , oxide , chemistry , pyridine n oxide , crystal engineering , organic chemistry , photochemistry , inorganic chemistry , materials science , crystal structure
To understand how deuterium and fluorine substituents influence the supramolecular architecture of pyridine N‐oxide crystals, the crystal structure of 3‐fluoropyridine N‐oxide (PNO‐3F) was determined and the crystal packing motives of non‐deuterated pyridine‐ N ‐oxide (PNO), partial‐deuterated pyridine‐ N ‐oxide (PNO‐D) and PNO‐3F were analyzed based on ab initio quantum‐chemical calculations of the intermolecular interaction energy, using the MP2/6‐311G(d,p) method. The appearance of the weak‐directing substituents deuterium and fluorine leads to significant changes in the crystal organization of the isotropic packing of PNO molecules.