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Title: Mechanistic study of styrene aziridination by iron( iv ) nitrides

Abstract

A combined experimental and computational investigation was undertaken to investigate the mechanism of aziridination of styrene by the tris(carbene)borate iron(IV) nitride complex, PhB(tBuIm)3FeN. While mechanistic investigations suggest that aziridination occurs via a reversible, stepwise pathway, it was not possible to confirm the mechanism using only experimental techniques. Density functional theory calculations support a stepwise radical addition mechanism, but suggest that a low-lying triplet (S = 1) state provides the lowest energy path for C–N bond formation (24.6 kcal mol-1) and not the singlet ground (S = 0) state. A second spin flip may take place in order to facilitate ring closure and the formation of the quintet (S = 2) aziridino product. A Hammett analysis shows that electron-withdrawing groups increase the rate of reaction σp (ρ = 1.2 ± 0.2). This finding is supported by the computational results, which show that the rate-determining step drops from 24.6 kcal mol-1 to 18.3 kcal mol-1 when (p-NO2C6H4)CHCH2 is used and slightly increases to 25.5 kcal mol-1 using (p-NMe2C6H4)CHCH2 as the substrate.

Authors:
 [1];  [2]; ORCiD logo [2]; ORCiD logo [3]
+ Show Author Affiliations
  1. Department of Chemistry, Indiana University, Bloomington, USA, Department of Chemistry
  2. Department of Chemistry, Indiana University, Bloomington, USA
  3. Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 34141, Republic of Korea, Department of Chemistry
Publication Date:
Research Org.:
New Mexico State Univ., Las Cruces, NM (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); Institute for Basic Science in Korea
OSTI Identifier:
1471749
Alternate Identifier(s):
OSTI ID: 1609964
Grant/Contract Number:  
FG02-08ER15996; IBS-R10-D1
Resource Type:
Published Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Name: Chemical Science Journal Volume: 9 Journal Issue: 45; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United Kingdom
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Crandell, Douglas W., Muñoz, Salvador B., Smith, Jeremy M., and Baik, Mu-Hyun. Mechanistic study of styrene aziridination by iron( iv ) nitrides. United Kingdom: N. p., 2018. Web. doi:10.1039/C8SC03677B.
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Crandell, Douglas W., Muñoz, Salvador B., Smith, Jeremy M., & Baik, Mu-Hyun. Mechanistic study of styrene aziridination by iron( iv ) nitrides. United Kingdom. https://doi.org/10.1039/C8SC03677B
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Crandell, Douglas W., Muñoz, Salvador B., Smith, Jeremy M., and Baik, Mu-Hyun. Wed . "Mechanistic study of styrene aziridination by iron( iv ) nitrides". United Kingdom. https://doi.org/10.1039/C8SC03677B.
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@article{osti_1471749,
title = {Mechanistic study of styrene aziridination by iron( iv ) nitrides},
author = {Crandell, Douglas W. and Muñoz, Salvador B. and Smith, Jeremy M. and Baik, Mu-Hyun},
abstractNote = {A combined experimental and computational investigation was undertaken to investigate the mechanism of aziridination of styrene by the tris(carbene)borate iron(IV) nitride complex, PhB(tBuIm)3FeN. While mechanistic investigations suggest that aziridination occurs via a reversible, stepwise pathway, it was not possible to confirm the mechanism using only experimental techniques. Density functional theory calculations support a stepwise radical addition mechanism, but suggest that a low-lying triplet (S = 1) state provides the lowest energy path for C–N bond formation (24.6 kcal mol-1) and not the singlet ground (S = 0) state. A second spin flip may take place in order to facilitate ring closure and the formation of the quintet (S = 2) aziridino product. A Hammett analysis shows that electron-withdrawing groups increase the rate of reaction σp (ρ = 1.2 ± 0.2). This finding is supported by the computational results, which show that the rate-determining step drops from 24.6 kcal mol-1 to 18.3 kcal mol-1 when (p-NO2C6H4)CHCH2 is used and slightly increases to 25.5 kcal mol-1 using (p-NMe2C6H4)CHCH2 as the substrate.},
doi = {10.1039/C8SC03677B},
journal = {Chemical Science},
number = 45,
volume = 9,
place = {United Kingdom},
year = {2018},
month = {11}
}
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    Fe‐Based Complexes as Styrene Aziridination Catalysts: Ligand Substitution Tunes Catalyst Activity
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