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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

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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, Vol. 133, No. 44, 25.10.2021, p. 24071-24077.

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, vol. 133, no. 44, pp. 24071-24077. https://doi.org/10.1002/ange.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, 133(44), 24071-24077. https://doi.org/10.1002/ange.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. 2021 Oct 25;133(44):24071-24077. Epub 2021 Oct 1. doi: 10.1002/ange.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. 2021 ; Vol. 133, No. 44. pp. 24071-24077.

Bibtex

@article{95df196fe09c4fa7ba5f08f13fc2f6d0,
title = "Mapping of N−C Bond Formation from a Series of Crystalline Peri‐Substituted Naphthalenes by Charge Density and Solid‐State NMR Methodologies",
abstract = "AbstractA combination of charge density studies and solid state nuclear magnetic resonance (NMR) 1JNC 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 sp2 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 1JNC couplings of ≈3–6 Hz for long C−N bonds (1.60–1.65 {\AA}), and 1JNC couplings of <1 Hz for N⋅⋅⋅C >2.1 {\AA}.",
keywords = "General Medicine",
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/ange.202111100",
language = "English",
volume = "133",
pages = "24071--24077",
journal = "Angewandte Chemie",
issn = "0044-8249",
publisher = "John Wiley & Sons, Ltd",
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 - AbstractA combination of charge density studies and solid state nuclear magnetic resonance (NMR) 1JNC 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 sp2 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 1JNC couplings of ≈3–6 Hz for long C−N bonds (1.60–1.65 Å), and 1JNC couplings of <1 Hz for N⋅⋅⋅C >2.1 Å.

AB - AbstractA combination of charge density studies and solid state nuclear magnetic resonance (NMR) 1JNC 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 sp2 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 1JNC couplings of ≈3–6 Hz for long C−N bonds (1.60–1.65 Å), and 1JNC couplings of <1 Hz for N⋅⋅⋅C >2.1 Å.

KW - General Medicine

U2 - 10.1002/ange.202111100

DO - 10.1002/ange.202111100

M3 - Journal article

VL - 133

SP - 24071

EP - 24077

JO - Angewandte Chemie

JF - Angewandte Chemie

SN - 0044-8249

IS - 44

ER -