Consequences of Curvature on Induced Magnetic Field: The Case of Helicenes.
aromaticity
electron delocalization
helicenes
magnetic responses
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
02 Jan 2020
02 Jan 2020
Historique:
received:
24
09
2019
pubmed:
5
11
2019
medline:
5
11
2019
entrez:
5
11
2019
Statut:
ppublish
Résumé
Helicenes consist of several fused rings twisted around an axis, forming a cylindrical helix, with π-delocalized electrons in the non-planar rings. Induced magnetic fields dissecting the orbital contributions of [6]-, [7]-, and [14]helicene are discussed. Computations show a deshielding cone produced by the π-electrons along the helical axis. Unexpectedly, the response of the core electrons produces a shielding cone, which is cumulative and sensitive to the curvature of the systems owing to the overlap of the other ring responses. A warning is provided regarding the evaluation of the delocalization in curved systems in which the x- and y-components of the induced magnetic field become relevant.
Identifiants
pubmed: 31680347
doi: 10.1002/chem.201904390
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
326-330Subventions
Organisme : Consejo Nacional de Ciencia y Tecnología
ID : CB-2015-252356
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
J. Meisenheimer, K. Witte, Ber. Dtsch. Chem. Ges. 1903, 36, 4153-4164.
Y. Shen, C.-F. Chen, Chem. Rev. 2012, 112, 1463-1535.
C.-F. Chen, Y. Shen, Structures and Properties of Helicenes. Helicene Chemistry, Springer, Berlin, 2017, pp. 19-40.
J. Barroso, F. Murillo, G. Martínez-Guajardo, F. Ortíz-Chi, S. Pan, M. A. Fernández-Herrera, G. Merino, Chem. Eur. J. 2018, 24, 11227-11233.
J. Barroso, J. L. Cabellos, S. Pan, F. Murillo, X. Zarate, M. A. Fernandez-Herrera, G. Merino, Chem. Commun. 2018, 54, 188-191.
A. Reisi-Vanani, A. A. Rezaei, J. Mol. Graphics Modell. 2015, 61, 85-88.
G. Portella, J. Poater, J. M. Bofill, P. Alemany, M. Solà, J. Org. Chem. 2005, 70, 4560.
J. M. Schulman, R. L. Disch, J Phys. Chem. A. 1999, 103, 6669-6672.
P. von Ragué Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318.
J. A. N. F. Gomes, Croat. Chem. Acta 1980, 53, 561-569.
J. Poater, J. M. Bofill, P. Alemany, M. Solà, J. Org. Chem. 2006, 71, 1700-1702.
A. Muñoz-Castro, Chem. Phys. Lett. 2011, 517, 113-115.
D. Sundholm, M. Rauhalahti, N. Özcan, R. Mera-Adasme, J. Kussmann, A. Luenser, C. Ochsenfeld, J. Chem. Theory Comput. 2017, 13, 1952-1962.
R. Gershoni-Poranne, Chem. Eur. J. 2018, 24, 4165-4172.
A. C. Castro, E. Osorio, J. O. C. Jiménez-Halla, E. Matito, W. Tiznado, G. Merino, J. Chem. Theory Comput. 2010, 6, 2701-2705.
G. Merino, T. Heine, G. Seifert, Chem. Eur. J. 2004, 10, 4367-4371.
T. Heine, R. Islas, G. Merino, J. Comput. Chem. 2007, 28, 302-309.
R. Islas, T. Heine, G. Merino, Acc. Chem. Res. 2012, 45, 215-228.
N. D. Charistos, A. G. Papadopoulos, M. P. Sigalas, J. Phys. Chem. A 2014, 118, 1113-1122.
Q. Xie, T. Sun, M. Orozco-Ic, J. Barroso, Y. Zhao, G. Merino, J. Zhu, Asian J. Org. Chem. 2019, 8, 123-127.
P. W. Fowler, C. M. Gibson, D. E. Bean, Proc. R. Soc. London Ser. A 2014, 470, 20130617.
S. Pelloni, P. Lazzeretti, J. Comput. Chem. 2018, 39, 21-34.
T. Heine, C. Corminboeuf, G. Seifert, Chem. Rev. 2005, 105, 3889-3910.
J. A. Pople, J. Chem. Phys. 1956, 24, 1111.
J. Jusélius, D. Sundholm, J. Gauss, J. Chem. Phys. 2004, 121, 3952-3963.
M. Ernzerhof, G. E. Scuseria, J. Chem. Phys. 1999, 110, 5029-5036.
C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158-6170.
S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys. 2010, 132, 154104.
M. Orozco-Ic, J. L. Cabellos, G. Merino, Aromagnetic, Cinvestav-Mérida, Mexico, 2016.
J. P. Perdew, J. A. Chevary, S. H. Vosko, K. A. Jackson, M. R. Pederson, D. J. Singh, C. Fiolhais, Phys. Rev. B 1992, 46, 6671-6687.
Gaussian 09, Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, H. Borkent, W. Laarhoven, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. J. Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski D. J. Fox, Gaussian, Inc. Wallingford CT, 2013.
E. D. Glendening, C. R. Landis, F. Weinhold, J. Comput. Chem. 2013, 34, 1429-1437.
P. Wolinski, J. F. Hinton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251-8260.
H. Fliegl, S. Taubert, O. Lehtonen, D. Sundholm, Phys. Chem. Chem. Phys. 2011, 13, 20500-20518.
R. Gershoni-Poranne, A. Stanger, Chem. Eur. J. 2014, 20, 5673-5688.
S. Klod, E. Kleinpeter, J. Chem. Soc. Perkin Trans. 2 2001, 1893-1898.
F. A. L. Anet, D. J. O'Leary, Concepts Magn. Reson. 1991, 3, 193-214.
A. G. Papadopoulos, N. D. Charistos, A. Muñoz-Castro, ChemPhysChem 2017, 18, 1499-1502.
G. Merino, M. Solá, Phys. Chem. Chem. Phys. 2016, 18, 11587-11588.