Iminophosphorane-substituted proton sponges. Part 2. Preparation and crystal structure of four phosphoranylideneammonionaphthalene derivatives
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 11,p. 1667-1676
- https://doi.org/10.1039/p29910001667
Abstract
Crystal structure analysis of salts of one monosubstituted (1) and three peri disubstituted naphthalene derivatives (2, 3 and 4) are described. The strong repulsion between the nitrogen lone pairs in neutral structures is replaced by an intramolecular N+–H ⋯ N interaction in compounds 2, 3 and 4 giving rise to a similar distortion in the naphthalene skeleton in each case, an inward bending of the exocyclic Caryl–N bonds and a decrease of the N ⋯ N distance: [2.606(4)–2.533(6)Å]versus 2.792(3)Å found in 1,8-bis(N,N-dimethyl)naphthalene and 2.716(11) and 2.739(10)Å in 1,8-diaminonaphthalene. This behaviour is characteristic of proton sponges.Keywords
This publication has 13 references indexed in Scilit:
- Iminophosphorane-substituted proton sponges. Part 1. X-ray molecular structures of 1,8-diaminonaphthalene and 1-amino-8-triphenylphosphoranylideneaminonaphthaleneJournal of the Chemical Society, Perkin Transactions 2, 1991
- [NH⋯N]+ and [NH⋯N]− intramolecular hydrogen bonds in the complex of 1,8-bis(dimethylamino)naphthalene with 1,8-bis(4-toluenesulphonamido)-2,4,5,7-tetranitronaphthaleneJournal of Molecular Structure, 1990
- SIR88 – a direct-methods program for the automatic solution of crystal structuresJournal of Applied Crystallography, 1989
- “Proton Sponges” and the Geometry of Hydrogen Bonds: Aromatic Nitrogen Bases with Exceptional BasicitiesAngewandte Chemie International Edition in English, 1988
- Systematic analysis of structural data as a research technique in organic chemistryAccounts of Chemical Research, 1983
- An empirical method for correcting diffractometer data for absorption effectsActa Crystallographica Section A Foundations of Crystallography, 1983
- Structure of benzyl(diethylamino)diphenylphosphonium chlorideActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1982
- Deformations around a bondJournal of Chemical Crystallography, 1979
- Peri interactions: an X-ray crystallographic study of the structure of 1,8-bis(dimethylaminonaphthalene)Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1973
- Normal probability plot analysis of error in measured and derived quantities and standard deviationsActa Crystallographica Section A, 1971