Computational Methods to Predict the Regioselectivity of Electrophilic Aromatic Substitution Reactions of Heteroaromatic Systems

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Computational Methods to Predict the Regioselectivity of Electrophilic Aromatic Substitution Reactions of Heteroaromatic Systems. / Kruszyk, Monika; Jessing, Mikkel; Kristensen, Jesper L; Jorgensen, Morten.

In: Journal of Organic Chemistry, Vol. 81, No. 12, 13.05.2016, p. 5128–5134.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Kruszyk, M, Jessing, M, Kristensen, JL & Jorgensen, M 2016, 'Computational Methods to Predict the Regioselectivity of Electrophilic Aromatic Substitution Reactions of Heteroaromatic Systems', Journal of Organic Chemistry, vol. 81, no. 12, pp. 5128–5134. https://doi.org/10.1021/acs.joc.6b00584

APA

Kruszyk, M., Jessing, M., Kristensen, J. L., & Jorgensen, M. (2016). Computational Methods to Predict the Regioselectivity of Electrophilic Aromatic Substitution Reactions of Heteroaromatic Systems. Journal of Organic Chemistry, 81(12), 5128–5134. https://doi.org/10.1021/acs.joc.6b00584

Vancouver

Kruszyk M, Jessing M, Kristensen JL, Jorgensen M. Computational Methods to Predict the Regioselectivity of Electrophilic Aromatic Substitution Reactions of Heteroaromatic Systems. Journal of Organic Chemistry. 2016 May 13;81(12):5128–5134. https://doi.org/10.1021/acs.joc.6b00584

Author

Kruszyk, Monika ; Jessing, Mikkel ; Kristensen, Jesper L ; Jorgensen, Morten. / Computational Methods to Predict the Regioselectivity of Electrophilic Aromatic Substitution Reactions of Heteroaromatic Systems. In: Journal of Organic Chemistry. 2016 ; Vol. 81, No. 12. pp. 5128–5134.

Bibtex

@article{4437f4d9b54a454db0f68606501f39b7,
title = "Computational Methods to Predict the Regioselectivity of Electrophilic Aromatic Substitution Reactions of Heteroaromatic Systems",
abstract = "The validity of calculated NMR shifts to predict the outcome of electrophilic aromatic substitution reactions on different heterocyclic compounds has been examined. Based on an analysis of >130 literature examples it was found that the lowest calculated 13C and/or 1H chemical shift of a heterocycle correlates qualitatively with the regiochemical outcome of halogenation reactions in >80% of the investigated cases. In the remaining cases, the site of electrophilic aromatic substitution can be explained by the calculated HOMO orbitals obtained using density functional theory. Using a combination of these two methods, the accuracy increases to >95%.",
author = "Monika Kruszyk and Mikkel Jessing and Kristensen, {Jesper L} and Morten Jorgensen",
year = "2016",
month = may,
day = "13",
doi = "10.1021/acs.joc.6b00584",
language = "English",
volume = "81",
pages = "5128–5134",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "12",

}

RIS

TY - JOUR

T1 - Computational Methods to Predict the Regioselectivity of Electrophilic Aromatic Substitution Reactions of Heteroaromatic Systems

AU - Kruszyk, Monika

AU - Jessing, Mikkel

AU - Kristensen, Jesper L

AU - Jorgensen, Morten

PY - 2016/5/13

Y1 - 2016/5/13

N2 - The validity of calculated NMR shifts to predict the outcome of electrophilic aromatic substitution reactions on different heterocyclic compounds has been examined. Based on an analysis of >130 literature examples it was found that the lowest calculated 13C and/or 1H chemical shift of a heterocycle correlates qualitatively with the regiochemical outcome of halogenation reactions in >80% of the investigated cases. In the remaining cases, the site of electrophilic aromatic substitution can be explained by the calculated HOMO orbitals obtained using density functional theory. Using a combination of these two methods, the accuracy increases to >95%.

AB - The validity of calculated NMR shifts to predict the outcome of electrophilic aromatic substitution reactions on different heterocyclic compounds has been examined. Based on an analysis of >130 literature examples it was found that the lowest calculated 13C and/or 1H chemical shift of a heterocycle correlates qualitatively with the regiochemical outcome of halogenation reactions in >80% of the investigated cases. In the remaining cases, the site of electrophilic aromatic substitution can be explained by the calculated HOMO orbitals obtained using density functional theory. Using a combination of these two methods, the accuracy increases to >95%.

U2 - 10.1021/acs.joc.6b00584

DO - 10.1021/acs.joc.6b00584

M3 - Journal article

C2 - 27176051

VL - 81

SP - 5128

EP - 5134

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 12

ER -

ID: 161390337