Precision X-ray Diffraction Study of the Secondary Interactions in the Crystal of 1-Dimethylcarbamoyl-8-Dimethylaminonaphthalene
- 1 January 1996
- journal article
- research article
- Published by Taylor & Francis in Molecular Crystals and Liquid Crystals
- Vol. 275 (1) , 241-254
- https://doi.org/10.1080/10587259608034078
Abstract
X-ray diffraction method has been used to study the structure and electron density distribution in the crystal of 1-dimethylcarbamoyl-8-dimethylaminonaphthalene. Attractive interaction between a nucleophilic nitrogen atom and an electrophilic carbon atom has been established. These atoms are at a distance of 2.71 Å which is much less than the sum of the Van der Waals radii (3.25 Å). A number of specific features in the deformation electron density maps are accounted for by this interaction. Comparative analysis of the structural features of the compound studied (along with theoretical calculations by MMP2 and MNDO methods) and a number of other naphthalene perisubstituted derivatives confirms the presence of the attractive interaction.Keywords
This publication has 7 references indexed in Scilit:
- Temperature dependence of thermal motion in crystalline naphthaleneActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1982
- Structural Studies of 1,8‐Disubstituted Naphthalenes as Probes for nucleophile‐electrophile interactionsHelvetica Chimica Acta, 1978
- Can X-ray data distinguish bonding effects from vibrational smearing?Acta Crystallographica Section A, 1976
- Stereoelectronic control in the cleavage of tetrahedral intermediates in the hydrolysis of esters and amidesTetrahedron, 1975
- Geometrical reaction coordinates. II. Nucleophilic addition to a carbonyl groupJournal of the American Chemical Society, 1973
- Least-squares refinement and the weighted difference synthesisActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1973
- On the rigid-body motion of molecules in crystalsActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1968