Iminophosphorane-substituted proton sponges. Part 3. Preparation and crystal structure of three salts of protonated 1-dimethylamino-8-triphenylphosphoranylideneammonionaphthalene
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 12,p. 2033-2040
- https://doi.org/10.1039/p29910002033
Abstract
Results of the crystal structure analysis of three 1-dimethylamino-8-triphenylphosphoranylideneammonionaphthalene salts are described. The ‘extra proton’ has been found to bind to the nitrogen atom of the iminophosphorane group, being engaged in a strong intramolecular contact [N ⋯ N = 2.519(3), 2.543(4), 2.571(6)Å; N–H ⋯ N = 154(6), 155(6) and 147(6)° for Br–, BF4 – and PF6 – salts, respectively] which is shorter in two salts than those displayed by the 1,8-bis(dimethylamino)naphthalene salts of Br–, BF4 – and TeOF5 –, which are considered as ‘proton sponges’[2.555(3), 2.562(2) and 2.574(3)Å, respectively].Keywords
This publication has 16 references indexed in Scilit:
- Iminophosphorane-substituted proton sponges. Part 2. Preparation and crystal structure of four phosphoranylideneammonionaphthalene derivativesJournal of the Chemical Society, Perkin Transactions 2, 1991
- 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
- Crystallographic studies on sterically affected chemical species Part II. Molecular and crystal structure of 1,8-bis(dimethylamino)- naphthalene tetrafluoroborate. Analysis of distortion of geometry in the aromatic part due to intramolecular hydrogen bondingJournal of Molecular Structure, 1990
- [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
- Structure and IR spectroscopic behaviour of 1,8-bis-(dimethylamino)naphthalene 2,4-dinitroimidazolateJournal of Molecular Structure, 1987
- A pentuply-bridging carbonyl group: crystal and molecular structure of a salt of the 1-oxo-2-phenyl-1,2-dicarbadodecaborate(12) anion, [LH]+[O(Ph)C2B10H10]–(L = 1,8-N,N,N′,N′-tetramethylnaphthalenediamine)Journal of the Chemical Society, Chemical Communications, 1987
- Systematic analysis of structural data as a research technique in organic chemistryAccounts of Chemical Research, 1983
- Sixty years of staudinger reactionTetrahedron, 1981
- Deformations around a bondJournal of Chemical Crystallography, 1979
- Crystal structures of the isomorphous tris(hexafluoroacetylacetonato)copper(II) and tris(hexafluoroacetylacetonato)magnesium salts of monoprotonated 1,8-bis(dimethylamino)naphthaleneJ. Chem. Soc., Dalton Trans., 1972