Triisopropylamine: Difference between revisions
Content deleted Content added
Jorge Stolfi (talk | contribs) Created stub from net refs. |
More info and refs. |
||
| Line 1: | Line 1: | ||
'''Triisopropylamine''' is an [[organic compound]] with formula C<sub>9</sub>H<sub>21</sub>N, consisting of three [[isopropyl]] |
'''Triisopropylamine''' is an [[organic compound]] (a [[tertiary amine]]) with formula C<sub>9</sub>H<sub>21</sub>N or N(C(CH<sub>3</sub>)<sub>2</sub>H)<sub>3</sub>, consisting of three [[isopropyl]] [[radical]]s bound to a [[nitrogen]] [[atom]].<ref>G. Graner, E. Hirota, T. Iijima, K. Kuchitsu, D. A. Ramsay, J. Vogt and N. Vogt (2003), ''C9H21N, Triisopropylamine''. In ''Molecules Containing Five or More Carbon Atoms'', volume 25D of the series ''Landolt-Börnstein - Group II Molecules and Radicals''. Springer-Verlag. ISBN 978-3-540-42860-2; DOI 10.1007/10735542_789.</ref><ref name="bock">Hans Bock, Ilka Goebel, Zdenek Havlas, Siegfried Liedle, Heinz Oberhammer (1991) ''Triisopropylamine: A Sterically Overcrowded Molecule with a Flattened NC3 Pyramid and a "p-Type" Nitrogen Electron Pair''. Angewandte Chemie International Edition in English, Volume 30 Issue 2, pages 187-190. DOI: 10.1002/anie.199101871. Also the issue's cover picture.</ref> It is a colorless liquid<ref name="halpern"/> that [[boiling point|boils at]] 47°C.<ref name="bock"/><ref>J.I.G. Codagan, John Buckingham, Finlay J. MacDonald, P. H. Rhodes (1996), ''Dictionary of organic compounds''</ref> |
||
In the early 1990s, theoretical studies and [[electron diffraction]] analysis of the 3D structure of the molecule, in the gas phase or in non-polar solvents, indicated that the bonds between the nitrogen atom and the three [[carbon]] atoms were nearly coplanar in the ground state, instead of forming a [[trigonal pyramid]] as in simpler amines.<ref name="halpern">Arthur M. Halpern, B. R. Ramachandran (1992), ''Photophysics of a sterically crowded tertiary-saturated amine: triisopropylamine''. J. Phys. Chem., vol. 96 (24), pp 9832–9839. DOI: 10.1021/j100203a047.</ref><ref>Christoph Kölmel, Christian Ochsenfeld and Reinhart Ahlrichs (1992), ''An ab initio investigation of structure and inversion barrier of triisopropylamine and related amines and phosphines''. Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta), Volume 82, Numbers 3-4</ref> The average C-N-C angle was caimed to be 119.2°,<ref name="bock"/> much closer to the 120° of the flat configuration than to the 111.8° of [[trimethylamine]]. However, in 1998 [[X-ray diffraction]] analysis of the crystallized solid claimed that the C<sub>3</sub>N core is actually pyramidal, with the N atom lying approximately 0.28 Å off the carbon's plane (whereas in trimethylamine the distance is about 0.45 Å). However the researchers could not rule out the [[crystal field effect]] as the cause of the asymmetry.<ref name="boese98">Boese, R.; Bläser, D.; Antipin, M. Y.; Chaplinski, V.; de Meijere, A. (1998) ''Non-planar structures of Et3N and Pri3N: a contradiction between the X-ray, and NMR and electron diffraction data for Pri3N.'' Chem. Commun. (Cambridge) 1998, 781–782. DOI: 10.1039/a708399h</ref> |
|||
The C-C-C planes of the isopropyl groups are slightly tilted (about 5°) relative to the threefold symmetry axis of the C<sub>3</sub>N core.<ref name="halpern"/><ref name="boese98"/> O<ref>Yang M, Albrecht-Schmitt T, Cammarata V, Livant P, Makhanu DS, Sykora R, and Zhu W (2009) ''Trialkylamines more planar at nitrogen than triisopropylamine in the solid state''. The Journal of organic chemistry 74(7):2671–2678. DOI:10.1021/jo802086h</ref> |
|||
Triisopropylamine can be prepared from [[diisopropylamine]] by a procedure developed by Bock and others.<ref name="bock"/> |
|||
==References== |
==References== |
||
Revision as of 01:11, 27 June 2009
Triisopropylamine is an organic compound (a tertiary amine) with formula C9H21N or N(C(CH3)2H)3, consisting of three isopropyl radicals bound to a nitrogen atom.[1][2] It is a colorless liquid[3] that boils at 47°C.[2][4]
In the early 1990s, theoretical studies and electron diffraction analysis of the 3D structure of the molecule, in the gas phase or in non-polar solvents, indicated that the bonds between the nitrogen atom and the three carbon atoms were nearly coplanar in the ground state, instead of forming a trigonal pyramid as in simpler amines.[3][5] The average C-N-C angle was caimed to be 119.2°,[2] much closer to the 120° of the flat configuration than to the 111.8° of trimethylamine. However, in 1998 X-ray diffraction analysis of the crystallized solid claimed that the C3N core is actually pyramidal, with the N atom lying approximately 0.28 Å off the carbon's plane (whereas in trimethylamine the distance is about 0.45 Å). However the researchers could not rule out the crystal field effect as the cause of the asymmetry.[6]
The C-C-C planes of the isopropyl groups are slightly tilted (about 5°) relative to the threefold symmetry axis of the C3N core.[3][6] O[7]
Triisopropylamine can be prepared from diisopropylamine by a procedure developed by Bock and others.[2]
References
- ^ G. Graner, E. Hirota, T. Iijima, K. Kuchitsu, D. A. Ramsay, J. Vogt and N. Vogt (2003), C9H21N, Triisopropylamine. In Molecules Containing Five or More Carbon Atoms, volume 25D of the series Landolt-Börnstein - Group II Molecules and Radicals. Springer-Verlag. ISBN 978-3-540-42860-2; DOI 10.1007/10735542_789.
- ^ a b c d Hans Bock, Ilka Goebel, Zdenek Havlas, Siegfried Liedle, Heinz Oberhammer (1991) Triisopropylamine: A Sterically Overcrowded Molecule with a Flattened NC3 Pyramid and a "p-Type" Nitrogen Electron Pair. Angewandte Chemie International Edition in English, Volume 30 Issue 2, pages 187-190. DOI: 10.1002/anie.199101871. Also the issue's cover picture.
- ^ a b c Arthur M. Halpern, B. R. Ramachandran (1992), Photophysics of a sterically crowded tertiary-saturated amine: triisopropylamine. J. Phys. Chem., vol. 96 (24), pp 9832–9839. DOI: 10.1021/j100203a047.
- ^ J.I.G. Codagan, John Buckingham, Finlay J. MacDonald, P. H. Rhodes (1996), Dictionary of organic compounds
- ^ Christoph Kölmel, Christian Ochsenfeld and Reinhart Ahlrichs (1992), An ab initio investigation of structure and inversion barrier of triisopropylamine and related amines and phosphines. Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta), Volume 82, Numbers 3-4
- ^ a b Boese, R.; Bläser, D.; Antipin, M. Y.; Chaplinski, V.; de Meijere, A. (1998) Non-planar structures of Et3N and Pri3N: a contradiction between the X-ray, and NMR and electron diffraction data for Pri3N. Chem. Commun. (Cambridge) 1998, 781–782. DOI: 10.1039/a708399h
- ^ Yang M, Albrecht-Schmitt T, Cammarata V, Livant P, Makhanu DS, Sykora R, and Zhu W (2009) Trialkylamines more planar at nitrogen than triisopropylamine in the solid state. The Journal of organic chemistry 74(7):2671–2678. DOI:10.1021/jo802086h
 | This chemistry-related article is a stub. You can help Wikipedia by expanding it. |