Crystal structures of o-, m,- and p-nitrophenylferrocenes and their relevance to other sterically crowded phenylferrocenes

Roger M G Roberts, Jack Silver, Bohari Mohd. Yamin, Michael G B Drew, Udo Eberhardt

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The crystal structures of the nitrophenylferrocenes [Fe(η-C5H5)(η-C5H4R)][R = o- (1), m- (2), or p-O2NC6H4 (3)] have been determined. All three structures consist of discrete molecules with the iron atom η5-bonded to both cyclopentadienyl rings with bond lengths in the range 1.997(9)-2.120(10) Å. The steric constraints of the nitro group lead to different conformations in the three structures. Thus in the ortho structure, the o-nitro group intersects the phenyl ring at angle (Θ′) of 42.3(1)° and the phenyl ring intersects the cyclopentadienyl (cp) ring at an angle (Θ) of 43.6(1)°. Corresponding angles in the less crowded meta and para structures are 10.3(1), 17.4(1) (meta) and 2.9(1), 12.5(1)° (para) respectively. These structures are discussed in conjunction with that of 2,2′,5,5′-tetramethyl-1,1′-bis(2″,4″,6″- trimethylphenyl)ferrocene, (4), and other ortho-substituted phenylferrocenes. Iron-57 Mössbauer and 13C n.m.r. data for (4) are presented and discussed. The 13C data have been used in an estimation of Θ for a number of ortho-substituted phenylferrocenes. A critical survey of known structures of ferrocene derivatives is also presented.

Original languageEnglish
Pages (from-to)1549-1556
Number of pages8
JournalJournal of the Chemical Society, Dalton Transactions
Issue number6
DOIs
Publication statusPublished - 1988

Fingerprint

Iron
Crystal structure
Bond length
Conformations
Derivatives
Atoms
Molecules
ferrocene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Crystal structures of o-, m,- and p-nitrophenylferrocenes and their relevance to other sterically crowded phenylferrocenes. / Roberts, Roger M G; Silver, Jack; Mohd. Yamin, Bohari; Drew, Michael G B; Eberhardt, Udo.

In: Journal of the Chemical Society, Dalton Transactions, No. 6, 1988, p. 1549-1556.

Research output: Contribution to journalArticle

@article{1d6b7d53dc48499591fb4cd6a04470a0,
title = "Crystal structures of o-, m,- and p-nitrophenylferrocenes and their relevance to other sterically crowded phenylferrocenes",
abstract = "The crystal structures of the nitrophenylferrocenes [Fe(η-C5H5)(η-C5H4R)][R = o- (1), m- (2), or p-O2NC6H4 (3)] have been determined. All three structures consist of discrete molecules with the iron atom η5-bonded to both cyclopentadienyl rings with bond lengths in the range 1.997(9)-2.120(10) {\AA}. The steric constraints of the nitro group lead to different conformations in the three structures. Thus in the ortho structure, the o-nitro group intersects the phenyl ring at angle (Θ′) of 42.3(1)° and the phenyl ring intersects the cyclopentadienyl (cp) ring at an angle (Θ) of 43.6(1)°. Corresponding angles in the less crowded meta and para structures are 10.3(1), 17.4(1) (meta) and 2.9(1), 12.5(1)° (para) respectively. These structures are discussed in conjunction with that of 2,2′,5,5′-tetramethyl-1,1′-bis(2″,4″,6″- trimethylphenyl)ferrocene, (4), and other ortho-substituted phenylferrocenes. Iron-57 M{\"o}ssbauer and 13C n.m.r. data for (4) are presented and discussed. The 13C data have been used in an estimation of Θ for a number of ortho-substituted phenylferrocenes. A critical survey of known structures of ferrocene derivatives is also presented.",
author = "Roberts, {Roger M G} and Jack Silver and {Mohd. Yamin}, Bohari and Drew, {Michael G B} and Udo Eberhardt",
year = "1988",
doi = "10.1039/DT9880001549",
language = "English",
pages = "1549--1556",
journal = "Journal of the Chemical Society, Dalton Transactions",
issn = "1472-7773",
publisher = "Royal Society of Chemistry",
number = "6",

}

TY - JOUR

T1 - Crystal structures of o-, m,- and p-nitrophenylferrocenes and their relevance to other sterically crowded phenylferrocenes

AU - Roberts, Roger M G

AU - Silver, Jack

AU - Mohd. Yamin, Bohari

AU - Drew, Michael G B

AU - Eberhardt, Udo

PY - 1988

Y1 - 1988

N2 - The crystal structures of the nitrophenylferrocenes [Fe(η-C5H5)(η-C5H4R)][R = o- (1), m- (2), or p-O2NC6H4 (3)] have been determined. All three structures consist of discrete molecules with the iron atom η5-bonded to both cyclopentadienyl rings with bond lengths in the range 1.997(9)-2.120(10) Å. The steric constraints of the nitro group lead to different conformations in the three structures. Thus in the ortho structure, the o-nitro group intersects the phenyl ring at angle (Θ′) of 42.3(1)° and the phenyl ring intersects the cyclopentadienyl (cp) ring at an angle (Θ) of 43.6(1)°. Corresponding angles in the less crowded meta and para structures are 10.3(1), 17.4(1) (meta) and 2.9(1), 12.5(1)° (para) respectively. These structures are discussed in conjunction with that of 2,2′,5,5′-tetramethyl-1,1′-bis(2″,4″,6″- trimethylphenyl)ferrocene, (4), and other ortho-substituted phenylferrocenes. Iron-57 Mössbauer and 13C n.m.r. data for (4) are presented and discussed. The 13C data have been used in an estimation of Θ for a number of ortho-substituted phenylferrocenes. A critical survey of known structures of ferrocene derivatives is also presented.

AB - The crystal structures of the nitrophenylferrocenes [Fe(η-C5H5)(η-C5H4R)][R = o- (1), m- (2), or p-O2NC6H4 (3)] have been determined. All three structures consist of discrete molecules with the iron atom η5-bonded to both cyclopentadienyl rings with bond lengths in the range 1.997(9)-2.120(10) Å. The steric constraints of the nitro group lead to different conformations in the three structures. Thus in the ortho structure, the o-nitro group intersects the phenyl ring at angle (Θ′) of 42.3(1)° and the phenyl ring intersects the cyclopentadienyl (cp) ring at an angle (Θ) of 43.6(1)°. Corresponding angles in the less crowded meta and para structures are 10.3(1), 17.4(1) (meta) and 2.9(1), 12.5(1)° (para) respectively. These structures are discussed in conjunction with that of 2,2′,5,5′-tetramethyl-1,1′-bis(2″,4″,6″- trimethylphenyl)ferrocene, (4), and other ortho-substituted phenylferrocenes. Iron-57 Mössbauer and 13C n.m.r. data for (4) are presented and discussed. The 13C data have been used in an estimation of Θ for a number of ortho-substituted phenylferrocenes. A critical survey of known structures of ferrocene derivatives is also presented.

UR - http://www.scopus.com/inward/record.url?scp=37049078102&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049078102&partnerID=8YFLogxK

U2 - 10.1039/DT9880001549

DO - 10.1039/DT9880001549

M3 - Article

SP - 1549

EP - 1556

JO - Journal of the Chemical Society, Dalton Transactions

JF - Journal of the Chemical Society, Dalton Transactions

SN - 1472-7773

IS - 6

ER -