Stabilization and Structure of the cis Tautomer of a Free-Base Porphyrin
Abstract
Single-crystal X-ray analysis of the β-heptakis(trifluoromethyl)-meso-tetrakis(p-fluorophenyl)porphyrin, H2[(CF3)7TpFPP], has revealed the first example of a stable cis tautomer of a free-base porphyrin, the long-postulated intermediate of porphyrin tautomerism. The stability of the unique molecule appears to reflect a dual origin: a strongly saddled porphyrin skeleton, which alleviates electrostatic repulsion between the two NH protons, and two polarization-enhanced, transannular N-H∙∙∙O-H∙∙∙N hydrogen bond chains, each involving a molecule of water. DFT calculations suggest that the observed tautomer has a lower energy than the alternative, doubly hydrated trans tautomer by some 8.3 kcal mol-1 . A fascinating prospect thus exists that H2[(CF3)7TpFPP]∙2H2O and cognate structures may act as supramolecular synthons, which, given their chirality, may even be amenable to resolution into optically pure enantiomers.
- Authors:
-
[1]
- The Arctic University of Norway, Tromso (Norway)
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Advanced Light Source (ALS)
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1436613
- Grant/Contract Number:
- AC02-05CH11231
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Angewandte Chemie (International Edition)
- Additional Journal Information:
- Journal Name: Angewandte Chemie (International Edition); Journal Volume: 56; Journal Issue: 34; Journal ID: ISSN 1433-7851
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Thomas, Kolle E., McCormick, Laura J., Vazquez-Lima, Hugo, and Ghosh, Abhik. Stabilization and Structure of the cis Tautomer of a Free-Base Porphyrin. United States: N. p., 2017.
Web. doi:10.1002/anie.201701965.
Thomas, Kolle E., McCormick, Laura J., Vazquez-Lima, Hugo, & Ghosh, Abhik. Stabilization and Structure of the cis Tautomer of a Free-Base Porphyrin. United States. doi:https://doi.org/10.1002/anie.201701965
Thomas, Kolle E., McCormick, Laura J., Vazquez-Lima, Hugo, and Ghosh, Abhik. Wed .
"Stabilization and Structure of the cis Tautomer of a Free-Base Porphyrin". United States. doi:https://doi.org/10.1002/anie.201701965. https://www.osti.gov/servlets/purl/1436613.
@article{osti_1436613,
title = {Stabilization and Structure of the cis Tautomer of a Free-Base Porphyrin},
author = {Thomas, Kolle E. and McCormick, Laura J. and Vazquez-Lima, Hugo and Ghosh, Abhik},
abstractNote = {Single-crystal X-ray analysis of the β-heptakis(trifluoromethyl)-meso-tetrakis(p-fluorophenyl)porphyrin, H2[(CF3)7TpFPP], has revealed the first example of a stable cis tautomer of a free-base porphyrin, the long-postulated intermediate of porphyrin tautomerism. The stability of the unique molecule appears to reflect a dual origin: a strongly saddled porphyrin skeleton, which alleviates electrostatic repulsion between the two NH protons, and two polarization-enhanced, transannular N-H∙∙∙O-H∙∙∙N hydrogen bond chains, each involving a molecule of water. DFT calculations suggest that the observed tautomer has a lower energy than the alternative, doubly hydrated trans tautomer by some 8.3 kcal mol-1 . A fascinating prospect thus exists that H2[(CF3)7TpFPP]∙2H2O and cognate structures may act as supramolecular synthons, which, given their chirality, may even be amenable to resolution into optically pure enantiomers.},
doi = {10.1002/anie.201701965},
journal = {Angewandte Chemie (International Edition)},
number = 34,
volume = 56,
place = {United States},
year = {2017},
month = {3}
}
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Figures / Tables:
Figure 1: Thermal ellipsoid plots (33%) of H2[(CF3)7TpFPP]·2H2O: (a) top view and (b) close-up of the porphyrin core with hydrogen bond distances (Å).
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Works referenced in this record:
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Works referencing / citing this record:
Crystal structure refinement with SHELXL
journal, January 2015
- Sheldrick, George M.
- Acta Crystallographica Section C Structural Chemistry, Vol. 71, Issue 1, p. 3-8
Structure and Stability of cis-Porphyrin
journal, January 1995
- Ghosh, Abhik; Almloef, Jan
- The Journal of Physical Chemistry, Vol. 99, Issue 4
Mechanism and Quantum Mechanical Tunneling Effects on Inner Hydrogen Atom Transfer in Free Base Porphyrin: A Direct ab Initio Dynamics Study
journal, February 2000
- Maity, Dilip K.; Bell, Robert L.; Truong, Thanh N.
- Journal of the American Chemical Society, Vol. 122, Issue 5
The role of porphyrin chemistry in tumor imaging and photodynamic therapy
journal, January 2011
- Ethirajan, Manivannan; Chen, Yihui; Joshi, Penny
- Chem. Soc. Rev., Vol. 40, Issue 1
Ab initio SCF studies of basis set effects in free base porphin
journal, November 1991
- Ghosh, Abhik; Almlöf, Jan; Gassman, Paul G.
- Chemical Physics Letters, Vol. 186, Issue 1
Nonplanar porphyrins and their significance in proteins
journal, January 1998
- A. Shelnutt, John; Song, Xing-Zhi; Ma, Jian-Guo
- Chemical Society Reviews, Vol. 27, Issue 1
CCDC 1501215: Experimental Crystal Structure Determination: TATQEN : 5,10,15,20-tetrakis(4-fluorophenyl)-2,3,7,8,12,13,17-heptakis(trifluoromethyl)porphyrin dihydrate
Space Group: P 21/c (14), Cell: a 14.3852(11)Å b 27.9206(18)Å c 11.9969(11)Å, α 90° β 104.213(6)° γ 90°
dataset, February 2017
- Thomas, Kolle E.; McCormick, Laura J.; Vazquez-Lima, Hugo
- The Cambridge Crystallographic Data Centre, vp
Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy
journal, January 2005
- Weigend, Florian; Ahlrichs, Reinhart
- Physical Chemistry Chemical Physics, Vol. 7, Issue 18, p. 3297-3305
Ab initio calculations on porphin
journal, November 1974
- Almlöf, Jan
- International Journal of Quantum Chemistry, Vol. 8, Issue 6
Supramolekulare Synthone für das Kristall-Engineering - eine neue organische Synthese
journal, November 1995
- Desiraju, Gautam R.
- Angewandte Chemie, Vol. 107, Issue 21
Chemistry with ADF
journal, January 2001
- te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J.
- Journal of Computational Chemistry, Vol. 22, Issue 9, p. 931-967
ShelXle : a Qt graphical user interface for SHELXL
journal, November 2011
- Hübschle, Christian B.; Sheldrick, George M.; Dittrich, Birger
- Journal of Applied Crystallography, Vol. 44, Issue 6
Rationale for mixing exact exchange with density functional approximations
journal, December 1996
- Perdew, John P.; Ernzerhof, Matthias; Burke, Kieron
- The Journal of Chemical Physics, Vol. 105, Issue 22, p. 9982-9985
Generalized Gradient Approximation Made Simple
journal, October 1996
- Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias
- Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868
Nonplanar distortion modes for highly substituted porphyrins
journal, December 1992
- Medforth, Craig J.; Senge, Mathias O.; Smith, Kevin M.
- Journal of the American Chemical Society, Vol. 114, Issue 25
NMR Study of the Tautomerism of Porphyrin Including the Kinetic HH/HD/DD Isotope Effects in the Liquid and the Solid State
journal, July 1994
- Braun, Juergen; Koecher, Martin; Schlabach, Martin
- Journal of the American Chemical Society, Vol. 116, Issue 15
“Strong” Hydrogen Bonds in Chemistry and Biology
journal, October 1997
- Perrin, Charles L.; Nielson, Jennifer B.
- Annual Review of Physical Chemistry, Vol. 48, Issue 1
The crystal and molecular structure of triclinic tetraphenylporphyrin
journal, June 1967
- Silvers, Stuart J.; Tulinsky, Alexander.
- Journal of the American Chemical Society, Vol. 89, Issue 13
Vibrational photochemistry of porphine imbedded in a hexane-d14 Shpol'skii matrix
journal, October 1990
- Butenhoff, Thomas J.; Chuck, Roy S.; Limbach, Hans Heinrich.
- The Journal of Physical Chemistry, Vol. 94, Issue 20
Primary kinetic HH/HD/DH/DD isotope effects and proton tunnelling in double proton-transfer reactions
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- Limbach, Hans-Heinrich; Hennig, J�rgen; Gerritzen, Detlef
- Faraday Discussions of the Chemical Society, Vol. 74
A Metallocorrole with Orthogonal Pyrrole Rings
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- Thomas, Kolle E.; Conradie, Jeanet; Hansen, Lars K.
- European Journal of Inorganic Chemistry, Vol. 2011, Issue 12
SHELXT – Integrated space-group and crystal-structure determination
journal, January 2015
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Electron correlation in tetrapyrroles: ab initio calculations on porphyrin and the tautomers of chlorin
journal, October 1993
- Almlof, Jan; Fischer, Thomas H.; Gassman, Paul G.
- The Journal of Physical Chemistry, Vol. 97, Issue 42
Octaiodoporphyrin
journal, November 2015
- Thomassen, Ivar K.; Vazquez-Lima, Hugo; Gagnon, Kevin J.
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Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis
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OH-Cluster mit circular angeordneten, homodromen Wasserstoffbrückenbindungen
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Hydrogen atom tunneling in the thermal tautomerism of porphine imbedded in a n-hexane matrix
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- Butenhoff, Thomas J.; Moore, C. Bradley.
- Journal of the American Chemical Society, Vol. 110, Issue 25
The Structure of free base Porphine: an Average of Three Independent Structures
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Arrhenius curves of hydrogen transfers: tunnel effects, isotope effects and effects of pre-equilibria
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- Philosophical Transactions of the Royal Society B: Biological Sciences, Vol. 361, Issue 1472
Die Wasserstoffbrücke im Festkörper
journal, January 2002
- Steiner, Thomas
- Angewandte Chemie, Vol. 114, Issue 1
OH Clusters with Homodromic Circular Arrangement of Hydrogen Bonds
journal, May 1980
- Saenger, Wolfram; Lindner, Klaus
- Angewandte Chemie International Edition in English, Vol. 19, Issue 5
Copper β-Octakis(trifluoromethyl)corroles: New Paradigms for Ligand Substituent Effects in Transition Metal Complexes
journal, November 2008
- Thomas, Kolle Ekaney; Wasbotten, Ingar H.; Ghosh, Abhik
- Inorganic Chemistry, Vol. 47, Issue 22
Two Macrocycles in One Shot: Synthesis, Spectroscopy, Photophysics, and Tautomerism of 23-Oxahemiporphycene and 21-Oxacorrole-5-carbaldehyde
journal, June 2018
- Ostapko, Jakub; Kelm, Anna; Kijak, Michał
- Chemistry - A European Journal, Vol. 24, Issue 39
Molecular structure of a gold β-octakis(trifluoromethyl)- meso -triarylcorrole: an 85° difference in saddling dihedral relative to copper
journal, April 2012
- Thomas, Kolle E.; Beavers, Christine M.; Ghosh, Abhik
- Molecular Physics, Vol. 110, Issue 19-20
The Hydrogen Bond in the Solid State
journal, January 2002
- Steiner, Thomas
- Angewandte Chemie International Edition, Vol. 41, Issue 1
Structure of tetra-n-propylporphine. Average structure for the free base macrocycle from three independent determinations
journal, June 1972
- Codding, Penelope W.; Tulinsky, A.
- Journal of the American Chemical Society, Vol. 94, Issue 12
Generalized Gradient Approximation Made Simple [Phys. Rev. Lett. 77, 3865 (1996)]
journal, February 1997
- Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias
- Physical Review Letters, Vol. 78, Issue 7
Photophysical and Structural Properties of Saddle-Shaped Free Base Porphyrins: Evidence for an “Orthogonal” Dipole Moment
journal, August 2001
- Sazanovich, Igor V.; Galievsky, Victor A.; van Hoek, Arie
- The Journal of Physical Chemistry B, Vol. 105, Issue 32
Redetermination of the structure of porphine
journal, June 1972
- Chen, Betty M. L.; Tulinsky, A.
- Journal of the American Chemical Society, Vol. 94, Issue 12
Two Macrocycles in One Shot: Synthesis, Spectroscopy, Photophysics, and Tautomerism of 23-Oxahemiporphycene and 21-Oxacorrole-5-carbaldehyde
journal, June 2018
- Ostapko, Jakub; Kelm, Anna; Kijak, Michał
- Chemistry - A European Journal, Vol. 24, Issue 39
Molekulares Engineering freier Porphyrinbasen als Liganden - das N-H⋅⋅⋅X-Bindungsmotiv in Tetrapyrrolen
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- Kielmann, Marc; Senge, Mathias O.
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Molecular Engineering of Free-Base Porphyrins as Ligands-The N−H⋅⋅⋅X Binding Motif in Tetrapyrroles
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Incremental Introduction of Organocatalytic Activity into Conformationally Engineered Porphyrins: Incremental Introduction of Organocatalytic Activity into Conformationally Engineered Porphyrins
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Porphyrins in troubled times: a spotlight on porphyrins and their metal complexes for explosives testing and CBRN defense
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Positive shift in corrole redox potentials leveraged by modest β-CF 3 -substitution helps achieve efficient photocatalytic C–H bond functionalization by group 13 complexes
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Free-base porphyrins with localized NH protons. Can substituents alone stabilize the elusive cis tautomer?
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- Thomas, Kolle E.; Conradie, Jeanet; Beavers, Christine M.
- Organic & Biomolecular Chemistry, Vol. 18, Issue 15
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