---
_id: '10392'
abstract:
- lang: eng
  text: Protonated formylmetallocenes [M(C5H5)(C5H4-CHOH)]+ (M = Fe, Ru) and their
    isomers have been studied at the BP86 and B3LYP levels of density functional theory.
    Oxygen-protonated isomers are the most stable forms in each case, with a plethora
    of ring- or metal-protonated species at least ca. 14 and 10 kcal/mol higher in
    energy for M = Fe and Ru, respectively. The computed rotational barriers around
    the C−C bond connecting the cyclopentadienyl and protonated formyl moieties, ca.
    18 kcal/mol, are indicative of substantial conjugation between these moieties.
    Some of the ring- and iron-protonated species are models for possible intermediates
    in Friedel–Crafts acylation of ferrocene, and the computations provide further
    evidence that exo attack is clearly favored over endo attack of the electrophile
    in this reaction. The structures of the most stable mono- and diprotonated formylferrocenes
    are corroborated by the good agreement between GIAO-B3LYP-computed and experimental
    NMR chemical shifts.
acknowledgement: M.B. wishes to thank Prof. W. Thiel and the Max-Planck-Institut für
  Kohlenforschung for continuing support. A Humboldt fellowship for V.V. is gratefully
  acknowledged. Computations were performed on Compaq XP1000 and ES40 workstations
  as well as on an Intel Xeon PC cluster at the MPI Mülheim. A.S. thanks the Computing
  Center of the University of Zagreb SRCE for allocating computer time on the Isabella
  cluster.
article_processing_charge: No
article_type: original
author:
- first_name: Anđela
  full_name: Šarić, Anđela
  id: bf63d406-f056-11eb-b41d-f263a6566d8b
  last_name: Šarić
  orcid: 0000-0002-7854-2139
- first_name: Valerije
  full_name: Vrček, Valerije
  last_name: Vrček
- first_name: Michael
  full_name: Bühl, Michael
  last_name: Bühl
citation:
  ama: Šarić A, Vrček V, Bühl M. Density functional study of protonated formylmetallocenes.
    <i>Organometallics</i>. 2008;27(3):394-401. doi:<a href="https://doi.org/10.1021/om700916f">10.1021/om700916f</a>
  apa: Šarić, A., Vrček, V., &#38; Bühl, M. (2008). Density functional study of protonated
    formylmetallocenes. <i>Organometallics</i>. American Chemical Society. <a href="https://doi.org/10.1021/om700916f">https://doi.org/10.1021/om700916f</a>
  chicago: Šarić, Anđela, Valerije Vrček, and Michael Bühl. “Density Functional Study
    of Protonated Formylmetallocenes.” <i>Organometallics</i>. American Chemical Society,
    2008. <a href="https://doi.org/10.1021/om700916f">https://doi.org/10.1021/om700916f</a>.
  ieee: A. Šarić, V. Vrček, and M. Bühl, “Density functional study of protonated formylmetallocenes,”
    <i>Organometallics</i>, vol. 27, no. 3. American Chemical Society, pp. 394–401,
    2008.
  ista: Šarić A, Vrček V, Bühl M. 2008. Density functional study of protonated formylmetallocenes.
    Organometallics. 27(3), 394–401.
  mla: Šarić, Anđela, et al. “Density Functional Study of Protonated Formylmetallocenes.”
    <i>Organometallics</i>, vol. 27, no. 3, American Chemical Society, 2008, pp. 394–401,
    doi:<a href="https://doi.org/10.1021/om700916f">10.1021/om700916f</a>.
  short: A. Šarić, V. Vrček, M. Bühl, Organometallics 27 (2008) 394–401.
date_created: 2021-11-29T15:31:06Z
date_published: 2008-01-15T00:00:00Z
date_updated: 2021-11-30T08:04:44Z
day: '15'
doi: 10.1021/om700916f
extern: '1'
intvolume: '        27'
issue: '3'
keyword:
- Inorganic Chemistry
- Organic Chemistry
- Physical and Theoretical Chemistry
language:
- iso: eng
main_file_link:
- url: https://pubs.acs.org/doi/10.1021/om700916f
month: '01'
oa_version: None
page: 394-401
publication: Organometallics
publication_identifier:
  eissn:
  - 1520-6041
  issn:
  - 0276-7333
publication_status: published
publisher: American Chemical Society
quality_controlled: '1'
scopus_import: '1'
status: public
title: Density functional study of protonated formylmetallocenes
type: journal_article
user_id: 8b945eb4-e2f2-11eb-945a-df72226e66a9
volume: 27
year: '2008'
...