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Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes: salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde

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Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes: salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde. / Lari, Alberth; Pitak, Matuesz B.; Coles, Simon J. et al.
In: Organic and Biomolecular Chemistry , Vol. 10, No. 38, 12.09.2012, p. 7763-7779.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Lari, A, Pitak, MB, Coles, SJ, Rees, GJ, Day, SP, Smith, ME, Hanna, JV & Wallis, JD 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 and Biomolecular Chemistry , vol. 10, no. 38, pp. 7763-7779. https://doi.org/10.1039/C2OB25929J

APA

Lari, A., Pitak, M. B., Coles, S. J., Rees, G. J., Day, S. P., Smith, M. E., Hanna, J. V., & 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 and Biomolecular Chemistry , 10(38), 7763-7779. https://doi.org/10.1039/C2OB25929J

Vancouver

Lari A, Pitak MB, Coles SJ, Rees GJ, Day SP, Smith ME et al. Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes: salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde. Organic and Biomolecular Chemistry . 2012 Sept 12;10(38):7763-7779. Epub 2012 Jul 13. doi: 10.1039/C2OB25929J

Author

Lari, Alberth ; Pitak, Matuesz B. ; Coles, Simon J. et al. / Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes : salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde. In: Organic and Biomolecular Chemistry . 2012 ; Vol. 10, No. 38. pp. 7763-7779.

Bibtex

@article{d810a83e63674693a7ab8c9bb15e4dcc,
title = "Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes: salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde",
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 {\AA} 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 {\AA}. The structural assignment of the former is supported by solid state 13C and 15N 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.",
author = "Alberth Lari and Pitak, {Matuesz B.} and Coles, {Simon J.} and Rees, {Gregory J.} and Day, {Stephen P.} and Smith, {Mark E.} and Hanna, {John V.} and Wallis, {John D.}",
year = "2012",
month = sep,
day = "12",
doi = "10.1039/C2OB25929J",
language = "English",
volume = "10",
pages = "7763--7779",
journal = "Organic and Biomolecular Chemistry ",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "38",

}

RIS

TY - JOUR

T1 - Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes

T2 - salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde

AU - Lari, Alberth

AU - Pitak, Matuesz B.

AU - Coles, Simon J.

AU - Rees, Gregory J.

AU - Day, Stephen P.

AU - Smith, Mark E.

AU - Hanna, John V.

AU - Wallis, John D.

PY - 2012/9/12

Y1 - 2012/9/12

N2 - 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 Å 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 Å. The structural assignment of the former is supported by solid state 13C and 15N 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.

AB - 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 Å 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 Å. The structural assignment of the former is supported by solid state 13C and 15N 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.

U2 - 10.1039/C2OB25929J

DO - 10.1039/C2OB25929J

M3 - Journal article

VL - 10

SP - 7763

EP - 7779

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 38

ER -