Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes: salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde
Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes: salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde
The X-ray crystal structures of salts and zwitterionic Knoevenagel products from 1-dimethylamino-naphthalene-8-carbaldehyde show long N-C bonds between peri-groups which provide models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes respectively. For the salts the N-C bonds lie in the range 1.625-1.638 angstrom with C-OH bonds intermediate in length between single and double bonds, while for the zwitterions the N-C bonds lie in the range 1.612-1.660 angstrom. The structural assignment of the former is supported by solid state C-13 and N-15 NMR studies on doubly isotopically-labelled material. Several zwitterions were converted to naphtha[1,8-bc]azepines by a mechanism involving the tertiary amino effect.
7763-7779
Lari, A
8b51b484-cb3b-43bf-b14d-f9ea76c455bb
Pitak, Mateusz
eeb6a00f-2291-4376-830f-d30dfd607ed1
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Rees, Gethin
09ff9c1c-61ff-4ab1-b3b9-364ce4223d90
Day, S.P.
28f85461-ad26-4557-88bc-08ba44c3fbed
Smith, M.E.
31d9a5fd-9d24-4037-a807-43e30ff3952c
Hanna, J.V.
fe8416bd-4401-44b9-8155-d1330234bef9
Wallis, J.D.
f31e8a77-e728-4c64-b8a1-4c998495697f
2012
Lari, A
8b51b484-cb3b-43bf-b14d-f9ea76c455bb
Pitak, Mateusz
eeb6a00f-2291-4376-830f-d30dfd607ed1
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Rees, Gethin
09ff9c1c-61ff-4ab1-b3b9-364ce4223d90
Day, S.P.
28f85461-ad26-4557-88bc-08ba44c3fbed
Smith, M.E.
31d9a5fd-9d24-4037-a807-43e30ff3952c
Hanna, J.V.
fe8416bd-4401-44b9-8155-d1330234bef9
Wallis, J.D.
f31e8a77-e728-4c64-b8a1-4c998495697f
Lari, A, Pitak, Mateusz, Coles, Simon J., Rees, Gethin, Day, S.P., Smith, M.E., Hanna, J.V. and Wallis, J.D.
(2012)
Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes: salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde.
Organic & Biomolecular Chemistry, 10 (38), .
(doi:10.1039/C2OB25929J).
Abstract
The X-ray crystal structures of salts and zwitterionic Knoevenagel products from 1-dimethylamino-naphthalene-8-carbaldehyde show long N-C bonds between peri-groups which provide models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes respectively. For the salts the N-C bonds lie in the range 1.625-1.638 angstrom with C-OH bonds intermediate in length between single and double bonds, while for the zwitterions the N-C bonds lie in the range 1.612-1.660 angstrom. The structural assignment of the former is supported by solid state C-13 and N-15 NMR studies on doubly isotopically-labelled material. Several zwitterions were converted to naphtha[1,8-bc]azepines by a mechanism involving the tertiary amino effect.
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Published date: 2012
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry, Faculty of Natural and Environmental Sciences
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Local EPrints ID: 345863
URI: http://eprints.soton.ac.uk/id/eprint/345863
ISSN: 1477-0520
PURE UUID: 1767d560-d014-4050-8f36-0b4d1b13ddb0
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Date deposited: 04 Dec 2012 17:35
Last modified: 15 Mar 2024 03:01
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Author:
A Lari
Author:
Mateusz Pitak
Author:
Gethin Rees
Author:
S.P. Day
Author:
M.E. Smith
Author:
J.V. Hanna
Author:
J.D. Wallis
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