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Mapping of N−C Bond Formation from a Series of Crystalline Peri‐Substituted Naphthalenes by Charge Density and Solid‐State NMR Methodologies

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

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Mapping of N−C Bond Formation from a Series of Crystalline Peri‐Substituted Naphthalenes by Charge Density and Solid‐State NMR Methodologies. / Rees, Gregory J.; Pitak, Mateusz B.; Lari, Alberth et al.
In: Angewandte Chemie International Edition, Vol. 60, No. 44, 25.10.2021, p. 23878-23884.

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

Harvard

Rees, GJ, Pitak, MB, Lari, A, Day, SP, Yates, JR, Gierth, P, Barnsley, K, Smith, ME, Coles, SJ, Hanna, JV & Wallis, JD 2021, 'Mapping of N−C Bond Formation from a Series of Crystalline Peri‐Substituted Naphthalenes by Charge Density and Solid‐State NMR Methodologies', Angewandte Chemie International Edition, vol. 60, no. 44, pp. 23878-23884. https://doi.org/10.1002/anie.202111100

APA

Rees, G. J., Pitak, M. B., Lari, A., Day, S. P., Yates, J. R., Gierth, P., Barnsley, K., Smith, M. E., Coles, S. J., Hanna, J. V., & Wallis, J. D. (2021). Mapping of N−C Bond Formation from a Series of Crystalline Peri‐Substituted Naphthalenes by Charge Density and Solid‐State NMR Methodologies. Angewandte Chemie International Edition, 60(44), 23878-23884. https://doi.org/10.1002/anie.202111100

Vancouver

Rees GJ, Pitak MB, Lari A, Day SP, Yates JR, Gierth P et al. Mapping of N−C Bond Formation from a Series of Crystalline Peri‐Substituted Naphthalenes by Charge Density and Solid‐State NMR Methodologies. Angewandte Chemie International Edition. 2021 Oct 25;60(44):23878-23884. Epub 2021 Oct 1. doi: 10.1002/anie.202111100

Author

Rees, Gregory J. ; Pitak, Mateusz B. ; Lari, Alberth et al. / Mapping of N−C Bond Formation from a Series of Crystalline Peri‐Substituted Naphthalenes by Charge Density and Solid‐State NMR Methodologies. In: Angewandte Chemie International Edition. 2021 ; Vol. 60, No. 44. pp. 23878-23884.

Bibtex

@article{c36d5242015a47fba51996974848122e,
title = "Mapping of N−C Bond Formation from a Series of Crystalline Peri‐Substituted Naphthalenes by Charge Density and Solid‐State NMR Methodologies",
abstract = "A combination of charge density studies and solid state nuclear magnetic resonance (NMR) 1 J NC coupling measurements supported by periodic density functional theory (DFT) calculations is used to characterise the transition from an n-π* interaction to bond formation between a nucleophilic nitrogen atom and an electrophilic sp 2 carbon atom in a series of crystalline peri-substituted naphthalenes. As the N⋅⋅⋅C distance reduces there is a sharp decrease in the Laplacian derived from increasing charge density between the two groups at ca. N⋅⋅⋅C = 1.8 {\AA}, with the periodic DFT calculations predicting, and heteronuclear spin-echo NMR measurements confirming, the 1 J NC couplings of ≈3-6 Hz for long C-N bonds (1.60-1.65 {\AA}), and 1 J NC couplings of <1 Hz for N⋅⋅⋅C >2.1 {\AA}. ",
keywords = "General Chemistry, Catalysis",
author = "Rees, {Gregory J.} and Pitak, {Mateusz B.} and Alberth Lari and Day, {Stephen P.} and Yates, {Jonathan R.} and Peter Gierth and Kristian Barnsley and Smith, {Mark E.} and Coles, {Simon J.} and Hanna, {John V.} and Wallis, {John D.}",
year = "2021",
month = oct,
day = "25",
doi = "10.1002/anie.202111100",
language = "English",
volume = "60",
pages = "23878--23884",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
publisher = "Wiley-VCH Verlag",
number = "44",

}

RIS

TY - JOUR

T1 - Mapping of N−C Bond Formation from a Series of Crystalline Peri‐Substituted Naphthalenes by Charge Density and Solid‐State NMR Methodologies

AU - Rees, Gregory J.

AU - Pitak, Mateusz B.

AU - Lari, Alberth

AU - Day, Stephen P.

AU - Yates, Jonathan R.

AU - Gierth, Peter

AU - Barnsley, Kristian

AU - Smith, Mark E.

AU - Coles, Simon J.

AU - Hanna, John V.

AU - Wallis, John D.

PY - 2021/10/25

Y1 - 2021/10/25

N2 - A combination of charge density studies and solid state nuclear magnetic resonance (NMR) 1 J NC coupling measurements supported by periodic density functional theory (DFT) calculations is used to characterise the transition from an n-π* interaction to bond formation between a nucleophilic nitrogen atom and an electrophilic sp 2 carbon atom in a series of crystalline peri-substituted naphthalenes. As the N⋅⋅⋅C distance reduces there is a sharp decrease in the Laplacian derived from increasing charge density between the two groups at ca. N⋅⋅⋅C = 1.8 Å, with the periodic DFT calculations predicting, and heteronuclear spin-echo NMR measurements confirming, the 1 J NC couplings of ≈3-6 Hz for long C-N bonds (1.60-1.65 Å), and 1 J NC couplings of <1 Hz for N⋅⋅⋅C >2.1 Å.

AB - A combination of charge density studies and solid state nuclear magnetic resonance (NMR) 1 J NC coupling measurements supported by periodic density functional theory (DFT) calculations is used to characterise the transition from an n-π* interaction to bond formation between a nucleophilic nitrogen atom and an electrophilic sp 2 carbon atom in a series of crystalline peri-substituted naphthalenes. As the N⋅⋅⋅C distance reduces there is a sharp decrease in the Laplacian derived from increasing charge density between the two groups at ca. N⋅⋅⋅C = 1.8 Å, with the periodic DFT calculations predicting, and heteronuclear spin-echo NMR measurements confirming, the 1 J NC couplings of ≈3-6 Hz for long C-N bonds (1.60-1.65 Å), and 1 J NC couplings of <1 Hz for N⋅⋅⋅C >2.1 Å.

KW - General Chemistry

KW - Catalysis

U2 - 10.1002/anie.202111100

DO - 10.1002/anie.202111100

M3 - Journal article

C2 - 34464506

VL - 60

SP - 23878

EP - 23884

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 44

ER -