Experimental and Theoretical Structure Elucidation of the [2 : 1] Complex Ion of Carbo[n]helicene with n=6, 7 and 8 and Ag
Energy-resolved CID
[2 : 1] helicene/silver(I) complex ion
carbo[n]helicenes
density functional calculations
tweezer
Journal
Chemphyschem : a European journal of chemical physics and physical chemistry
ISSN: 1439-7641
Titre abrégé: Chemphyschem
Pays: Germany
ID NLM: 100954211
Informations de publication
Date de publication:
02 Nov 2023
02 Nov 2023
Historique:
revised:
12
08
2023
received:
05
08
2023
medline:
14
8
2023
pubmed:
14
8
2023
entrez:
14
8
2023
Statut:
ppublish
Résumé
Gas-phase complexes of [n]helicenes with n=6, 7 and 8 and the silver(I) cation are generated utilizing electrospray ionization mass spectrometry (ESI-MS). Besides the well-established [1 : 1] helicene/Ag
Identifiants
pubmed: 37578805
doi: 10.1002/cphc.202300496
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300496Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : 182849149
Informations de copyright
© 2023 The Authors. ChemPhysChem published by Wiley-VCH GmbH.
Références
Y.-M. Chen, P. Armentrout, Chem. Phys. Lett. 1993, 210, 123-128.
Y.-M. Chen, P. B. Armentrout, J. Phys. Chem. 1995, 99, 11424-11431.
N. L. Ma, K. M. Ng, C. W. Tsang, Chem. Phys. Lett. 1997, 277, 306-310.
Y.-P. Ho, Y.-C. Yang, S. J. Klippenstein, R. C. Dunbar, J. Phys. Chem. A 1997, 101, 3338-3347.
E. Bayer, P. Gfrörer, C. Rentel, Angew. Chem. Int. Ed. 1999, 38, 992-995.
M. J. Manard, P. R. Kemper, M. T. Bowers, Int. J. Mass Spectrom. 2005, 241, 109-117.
J. A. Maner, D. T. Mauney, M. A. Duncan, J. Phys. Chem. Lett. 2015, 6, 4493-4498.
P. Motloch, J. Jašík, J. Roithová, Organometallics 2021, 40, 1492-1502.
P. Kebarle, U. H. Verkerk, Mass Spectrom. Rev. 2009, 28, 898-917.
IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans, International Agency for Research on Cancer 1983.
C. Li, M. Liu, N. G. Pschirer, M. Baumgarten, K. Müllen, Chem. Rev. 2010, 110, 6817-6855.
T. M. Figueira-Duarte, K. Müllen, Chem. Rev. 2011, 111, 7260-7314.
S. Günes, H. Neugebauer, N. S. Sariciftci, Chem. Rev. 2007, 107, 1324-1338.
A. C. Arias, J. D. MacKenzie, I. McCulloch, J. Rivnay, A. Salleo, Chem. Rev. 2010, 110, 3-24.
A. C. Grimsdale, K. Leok Chan, R. E. Martin, P. G. Jokisz, A. B. Holmes, Chem. Rev. 2009, 109, 897-1091.
R. M. Duke, E. B. Veale, F. M. Pfeffer, P. E. Kruger, T. Gunnlaugsson, Chem. Soc. Rev. 2010, 39, 3936-3953.
Y. N. Teo, E. T. Kool, Chem. Rev. 2012, 112, 4221-4245.
Y. Yang, Q. Zhao, W. Feng, F. Li, Chem. Rev. 2013, 113, 192-270.
K. M. Ng, N. L. Ma, C. W. Tsang, Rapid Commun. Mass Spectrom. 1998, 12, 1679-1684.
M. Takino, S. Daishima, K. Yamaguchi, T. Nakahara, J. Chromatogr. A 2001, 928, 53-61.
S. G. Roussis, R. Proulx, Anal. Chem. 2002, 74, 1408-1414.
K. Ming Ng, N. Ling Ma, C. Wai Tsang, Rapid Commun. Mass Spectrom. 2003, 17, 2082-2088.
K. K. Laali, S. Hupertz, A. G. Temu, S. E. Galembeck, Org. Biomol. Chem. 2005, 3, 2319-2326.
E. P. Maziarz III, G. A. Baker, T. D. Wood, Can. J. Chem. 2005, 83, 1871-1877.
M. Savoca, T. Wende, L. Jiang, J. Langer, G. Meijer, O. Dopfer, K. R. Asmis, J. Phys. Chem. Lett. 2011, 2, 2052-2056.
T. Ghislain, P. Faure, R. Michels, J. Am. Soc. Mass Spectrom. 2012, 23, 530-536.
M. Eftekhari, A. I. Ismail, R. N. Zare, Rapid Commun. Mass Spectrom. 2012, 26, 1985-1992.
S. Liu, A. Y. Rogachev, ChemPhysChem. 2018, 19, 2579-2588.
C. M. Havrilla, D. L. Hachey, N. A. Porter, J. Am. Chem. Soc. 2000, 122, 8042-8055.
H. Yin, D. L. Hachey, N. A. Porter, J. Am. Soc. Mass Spectrom. 2001, 12, 449-455.
J. R. Seal, C. M. Havrilla, N. A. Porter, D. L. Hachey, J. Am. Soc. Mass Spectrom. 2003, 14, 872-880.
H. Deng, P. Kebarle, J. Org. Chem. 1998, 102, 571-579.
C. Jackschath, I. Rabin, W. Schulze, Z. Phys. D 1992, 22, 517-520.
R. H. Martin, Angew. Chem. Int. Ed. 1992, 86, 727-738.
Y. Shen, C.-F. Chen, Chem. Rev. 2012, 112, 1463-1535.
N. Saleh, C. Shen, J. Crassous, Chem. Sci. 2014, 5, 3680-3694.
M. Gingras, G. Félix, R. Peresutti, Chem. Soc. Rev. 2013, 42, 1007-1050.
M. Gingras, Chem. Soc. Rev. 2013, 42, 1051-1095.
M. Gingras, Chem. Soc. Rev. 2013, 42, 968-1006.
S. Obenland, W. Schmidt, J. Am. Chem. Soc. 1975, 97, 6633-6638.
R. C. Dougherty, J. Am. Chem. Soc. 1968, 90, 5788-5793.
K. K. Laali, J. J. Houser, J. Chem. Soc. Perkin Trans. 2 1994, 6, 1303-1308.
M. J. Fuchter, J. Schaefer, D. K. Judge, B. Wardzinski, M. Weimar, I. Krossing, Dalton Trans. 2012, 41, 8238-8241.
E. Makrlík, J. Jaklová Dytrtová, P. Vaňura, J. Sýkora, C. Vladimír, J. Storch, Chem. Phys. Lett. 2015, 633, 105-108.
B. Klepetářová, E. Makrlík, D. Sýkora, S. Böhm, P. Vaňura, Polyhedron 2016, 117, 1-6.
E. Makrlík, B. Klepetářová, D. Sýkora, S. Böhm, P. Vaňura, J. Storch, Chem. Phys. Lett. 2015, 635, 355-359.
S. Böhm, E. Makrlík, P. Vaňura, B. Klepetářová, D. Sýkora, Monatsh. Chem. 2015, 146, 1795-1798.
A. O. Ortolan, G. F. Caramori, R. L. T. Parreira, A. Muñoz-Castro, ChemPhysChem. 2018, 19, 2321-2330.
M. Calama, D. Reinhoudt, N. M. Nibbering, Chem. Commun. 1998, 9, 1021-1022.
K. A. Jolliffe, M. C. Calama, R. Fokkens, N. M. M. Nibbering, P. Timmerman, D. N. Reinhoudt, Angew. Chem. Int. Ed. 1998, 37, 1247-1251.
J. Mucelini, I. Østrøm, A. O. Ortolan, K. F. Andriani, G. F. Caramori, R. L. Parreira, K. K. Laali, Dalton Trans. 2019, 48, 13281-13292.
P. C. Burgers, J. L. Holmes, J. K. Terlouw, Eur. J. Mass Spectrom. 2016, 22, 297-305.
Q. Duez, N. A. van Huizen, V. Lemaur, J. De Winter, J. Cornil, P. C. Burgers, P. Gerbaux, Int. J. Mass Spectrom. 2019, 435, 34-41.
G. W. Breton, J. Phys. Org. Chem. 2022, 35, e4301.
M. Kinzelmann, J. Oschwald, H. Elsen, V. Warmbrumm, M. Hauschild, S. Harder, M. Kivala, T. Drewello, Phys. Chem. Chem. Phys. 2023, 25, 15382-15390.
M. Roy, V. Berezhnaia, M. Villa, N. Vanthuyne, M. Giorgi, J.-V. Naubron, S. Poyer, V. Monnier, L. Charles, Y. Carissan, D. Hagebaum-Reignier, J. Rodriguez, M. Gingras, Y. Coquerel, Angew. Chem. Int. Ed. 2020, 59, 3264-3271.
D. Fati, Y. V. Vasil'ev, N. K. Wachter, R. Taylor, T. Drewello, Int. J. Mass Spectrom. 2003, 229, 3-10.
R. W. Kirschbaum, D. Prenzel, S. Frankenberger, R. R. Tykwinski, T. Drewello, J. Org. Chem. 2015, 119, 2861-2870.
J. Míšek, M. Tichý, I. G. Stará, I. Starý, D. Schröder, Collect. Czech. Chem. Commun. 2009, 74, 323-333.
R. Ahlrichs, M. Bär, M. Häser, H. Horn, C. Kölmel, Chem. Phys. Lett. 1989, 162, 165-169.
Turbomole V7.2 2017, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH 1989-2007, TURBOMOLE GmbH, since 2007.
J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865.
F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys. 2010, 132, 154104.
B. P. Pozniak, R. C. Dunbar, J. Am. Chem. Soc. 1997, 119, 10439-10445.
T. M. Kertesz, L. H. Hall, D. W. Hill, D. F. Grant, J. Am. Soc. Mass Spectrom. 2009, 20, 1759-1767.
D. W. Hill, C. L. Baveghems, D. R. Albaugh, T. M. Kormos, S. Lai, H. K. Ng, D. F. Grant, Rapid Commun. Mass Spectrom. 2012, 26, 2303-2310.
R. W. Kirschbaum, M. Hausmann, O. V. Boltalina, S. H. Strauss, T. Drewello, Phys. Chem. Chem. Phys. 2015, 17, 23052-23058.
J. F. Hitzenberger, P. O. Dral, U. Meinhardt, T. Clark, W. Thiel, M. Kivala, T. Drewello, ChemPlusChem. 2017, 82, 204-211.
J.-F. Gal, Chem. Phys. Lett. 2017, 680, 28-30.
R. Arakawa, M. Kobayashi, T. Nishimura, J. Mass Spectrom. 2000, 35, 178-182.
X. Wang, H. Becker, A. C. Hopkinson, R. E. March, L. T. Scott, D. K. Böhme, Int. J. Mass Spectrom. Ion Processes 1997, 161, 69-76.
A. I. S. Holm, H. A. B. Johansson, H. Cederquist, H. Zettergren, J. Chem. Phys. 2011, 134, 044301.
B. J. West, L. Lesniak, P. M. Mayer, J. Org. Chem. 2019, 123, 3569-3574.
D. Schröder, J. Loos, H. Schwarz, R. Thissen, D. V. Preda, L. T. Scott, D. Caraiman, M. V. Frach, D. K. Böhme, Helv. Chim. Acta 2001, 84, 1625-1634.
J. W. Buchanan, G. A. Grieves, N. D. Flynn, M. A. Duncan, Int. J. Mass Spectrom. 1999, 185-187, 617-624.
S. P. Ekern, A. G. Marshall, J. Szczepanski, M. Vala, J. Org. Chem. 1998, 102, 3498-3504.
X. Guo, H. L. Sievers, H. F. Grützmacher, Int. J. Mass Spectrom. 1999, 185, 1-10.
F. Gámez, A. R. Hortal, B. Martínez-Haya, J. Soltwisch, K. Dreisewerd, J. Mass Spectrom. 2014, 49, 1127-1138.
I. J. Webster, J. L. Beckham, N. D. Johnson, M. A. Duncan, J. Org. Chem. 2022, 126, 1144-1157.
A. E. Pomerantz, Q. Wu, O. C. Mullins, R. N. Zare, Energy Fuels 2015, 29, 2833-2842.
K. Y. Amsharov, M. A. Kabdulov, M. Jansen, Eur. J. Org. Chem. 2009, 36, 6328-6335.
S. Fujino, M. Yamaji, H. Okamoto, T. Mutai, I. Yoshikawa, H. Houjou, F. Tani, Photochem. Photobiol. Sci. 2017, 16, 925-934.