Structural diversity in the solid-state architectures of bis(4-pyridyl)acetylene and its derivatives
Article Sidebar
Accepted 2020-02-01
Published 2020-03-31
Main Article Content
Abstract
The crystals of bis(4-pyridyl)acetylene are orthorhombic and belong to the space group Fddd. Solid-state investigation using conventional and Hirshfeld analytical techniques revealed valuable data and structural diversities that explain the wide gap between established crystal reports of co-crystals and metal organic frameworks and the pure form of the title compound. Hirshfeld surface analysis in this wise has proved to be a useful tool in unravelling complex intermolecular interactions and simplifying them at the 2D and 3D levels using sub-tools such as fingerprint plots and electrostatic potential surfaces. Both techniques have shown that the H∙∙∙Npyr interactions in the title compound are shorter than those in its polymorphic counterpart by 0.2 Å. The more stable network provided by hetero-molecular interactions in co-crystals and metal complexes of bis(4-pyridyl)acetylene shed light on their lengthy existence compared to the less favorable homo-molecular interactions in pure molecules of bis(4-pyridyl)acetylene.
This Abstract was viewed 2242 times |
Article PDF downloaded 755 times
Article CIF FILE downloaded 0 times
Article Details
[1]. Yu, B.; Tracey, J. I.; Cheng, Z.; Vacha, M.; O'Carroll, D. M. Phys. Chem. Chem. Phys. 2018, 20, 11749-11757.
https://doi.org/10.1039/C8CP01314D
[2]. Qi, M.; Hulsmann, M.; Godt, A. J. Org. Chem. 2016, 81, 2549-2571.
https://doi.org/10.1021/acs.joc.6b00125
[3]. Pearce, T. R.; Waybrant, B.; Kokkoli, E. Chem. Commun. 2014, 50, 210-212.
https://doi.org/10.1039/C3CC42311E
[4]. Meineke, D. N. H.; Bossi, M. L.; Ta, H.; Belov, V. N.; Hell, S. W. Chem. Eur. J. 2017, 23, 2469-2475.
https://doi.org/10.1002/chem.201605587
[5]. Liese, S.; Netz, R. R. Beilstein J. Org. Chem. 2015, 11, 804-816.
https://doi.org/10.3762/bjoc.11.90
[6]. Rupert, B.; Paoli, M. D.; Rupert, B. L.; Mitchell, W. J.; Ferguson, A. J.; Muhammet, E. K.; Rance, W. L.; Rumbles, G.; Ginley, D. S.; Shaheen, S. E.; Kopidakis, N. J. Mater. Chem. 2009, 19, 5311-5324.
https://doi.org/10.1039/b903427g
[7]. Cann, J.; Dayneko, S.; Sun, J.; Hendsbee, A. D.; Hill, I. G.; Welch, G. C. J. Mater. Chem. C 2017, 5, 2074-2083.
https://doi.org/10.1039/C6TC05107C
[8]. Antina, E. V.; Guseva, G. B.; Loginova, A. E.; Semeikin, A. S.; V'yugin, A. I. Russ. J. Gen. Chem. 2010, 80, 2374-2381.
https://doi.org/10.1134/S107036321011023X
[9]. Rajakumar, P.; Visalakshi, K. Arkivoc, 2011, 10, 213-220.
https://doi.org/10.3998/ark.5550190.0012.a17
[10]. Huang, R.; Chiu, Y.; Chang, Y.; Chen, K.; Huang, P.; Chiang, T.; Chang, Y. J. New J. Chem. 2017, 41, 8016-8025.
https://doi.org/10.1039/C7NJ00413C
[11]. Dallos, T.; Beckmann, D.; Brunklaus, G.; Baumgarten, M. J. Am. Chem. Soc. 2011, 133, 13898-13901.
https://doi.org/10.1021/ja2057709
[12]. Ni, Z.; Liu, J.; Hoque, M. N.; Liu, W.; Li, J.; Chen, Y.; Tong, M. Coord. Chem. Rev. 2017, 335, 28-43.
https://doi.org/10.1016/j.ccr.2016.12.002
[13]. Fenenko, L.; Shao, G.; Orita, A.; Yahiro, M.; Otera, J.; Svechniko, S.; Adachi, C. Chem. Commun. 2007, 2278-2280.
https://doi.org/10.1039/b700466d
[14]. Mahmoudpour, A.; Nafisi, S.; Najafi, E.; and Notash, B.; Main Gr. Met. Chem. 2019, 42, 51-59.
https://doi.org/10.1515/mgmc-2019-0005
[15]. Faukner, T.; Slany, L.; Sloufova, I.; Vohlidal, J.; Zednik, J. Macromol. Res. 2016, 24, 441-449.
https://doi.org/10.1007/s13233-016-4062-0
[16]. Shi, L.; Guo, Y.; Hu, W.; Liu, Y.; Mater. Chem. Front. 2017, 1, 2423-2456.
https://doi.org/10.1039/C7QM00169J
[17]. Seth, S.; Matzger, A. J. Cryst. Growth. Des. 2017, 17, 4043-4048.
https://doi.org/10.1021/acs.cgd.7b00808
[18]. Yuan, S.; Zou, L.; Qin, J.; Li, J.; Huang, L.; Feng, L.; Wang, X.; Bosch, M. Nat. Commun. 2017, 8, 1-10.
https://doi.org/10.1038/ncomms15356
[19]. Yang, X.; Xu, Q. Cryst. Growth. Des. 2017, 17, 1450-1455.
https://doi.org/10.1021/acs.cgd.7b00166
[20]. Dankhoff, K.; Lochenie, C.; Puchtler, F.; Weber, B. Eur. J. Inorg. Chem. 2016, 2016, 2136-2143.
https://doi.org/10.1002/ejic.201501175
[21]. Bajpai, A.; Scott, H. S.; Pham, T.; Chen, K.; Space, B.; Lusi, M.; Perry, M. L.; Zaworotko, M. J. IUCrJ 2016, 3, 430-439.
https://doi.org/10.1107/S2052252516015633
[22]. Dias, S. I. G.; S. Rabac, I. C. Santos, D. Wallis, and M. Almeida, Cryst. Eng. Comm. 2010, 12, 3397-3400.
https://doi.org/10.1039/c003838e
[23]. Carlucci, L.; Ciani, G.; Macchi, P.; Proserpio, D. M. Chem. Commun. 1998, 1, 1837-1838.
https://doi.org/10.1039/a803662d
[24]. Bosch, E. Cryst. Growth. Des. 2010, 10, 3808-3813, .
https://doi.org/10.1021/cg100707y
[25]. Beckmann, J.; Janicke, S. L. Eur. J. Inorg. Chem. 2006, 2006, 3351-3358.
https://doi.org/10.1002/ejic.200600383
[26]. Bartual-murgui, C.; Ortega-Villar, N. A.; Shepherd, H. J.; Munoz, C. M.; Salmon, L.; Bousseksou, A.; Real, J. A. J. Mater. Chem. 2011, 21, 7217-7222.
https://doi.org/10.1039/c0jm04387g
[27]. Tsaggeos, K.; Masiera, N.; Niwicka, A.; Dokorou, V.; Siskos, M. G.; Skoulika, S.; Michaelides, A. Cryst. Growth. Des. 2012, 12, 2187-2194.
https://doi.org/10.1021/cg200681s
[28]. Wang, C.; Batsanov, A. S.; Bryce, M. R.; Martın, S.; Nichols, R. J.; Higgins, S. J.; Suarez, V. M.; Lambert, C. J. J. Am. Chem. Soc. 2009, 131, 15647-15654.
https://doi.org/10.1021/ja9061129
[29]. Sokolov, A. N.; Tomislav, F.; Blais, S.; Ripmeester, J. A.; Macgillivray, L. R. Cryst. Growth. Des. 2006, 6, 2427-2428.
https://doi.org/10.1021/cg0605133
[30]. Ryu, J. Y.; Lee, J. M.; Park, Y. J.; Van Nghia, N.; Lee, M. H.; Lee, J. Organometallics 2013, 32, 7272-7274.
https://doi.org/10.1021/om401145s
[31]. Neogi, S.; Lorenz, Y.; Engeser, M.; Samanta, D.; Schmittel, M. Inorg. Chem. 2013, 52, 6975-6984.
https://doi.org/10.1021/ic400328d
[32]. Desiraju, G. R. J. Am. Chem. Soc. 2013, 135, 9952-9967.
https://doi.org/10.1021/ja403264c
[33]. Choua, S.; Jouaiti, A.; Geoffroy, M. Phys. Chem. Chem. Phys. 1999, 1, 3557-3560.
https://doi.org/10.1039/a902689d
[34]. Zaman, B.; Tomura, M.; Yamashita, Y. J. Org. Chem. 2001, 66, 5987-5995.
https://doi.org/10.1021/jo001746i
[35]. Marin, G.; Andruh, M.; Madalan, A. M.; Blake, A. J.; Wilson, C.; Champness, N. R.; Schroder, M. Cryst. Growth. Des. 2008, 8, 964-975.
https://doi.org/10.1021/cg700879q
[36]. Elacqua, E.; Bucar, D. -K.; Henry, R. F.; Zhang, G. G. Z.; Macgillivray, L. R. Cryst. Growth. Des. 2013, 13, 393-403.
https://doi.org/10.1021/cg301745x
[37]. Tanner, M.; Ludi, A. Chimica 1980, 34, 23-24.
https://doi.org/10.1080/10464883.1980.10758631
[38]. Sheldrick, G. M. Acta. Cryst. Sect. A 2007, 64, 112-122.
https://doi.org/10.1107/S0108767307043930
[39]. Boere, R. T.; Roemmele, T. L.; Yu, X. Inorg. Chem. 2011, 50, 5123-5136.
https://doi.org/10.1021/ic2003996
[40]. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; Streek, J. V.; Wood, P. A. J. Appl. Cryst. 2008, 41, 466-470.
https://doi.org/10.1107/S0021889807067908
[41]. Turner, M. J.; McKinnon, J. J.; Wolff, S. K.; Grimwood, D. J.; Spackman, P. R.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer17, University of Western Australia, 2017.
[42]. BioCIS UMR-CNRS-8076, Universite de Paris-Saclay, France, Retrieved Feb 01, 2020, from https://www.sigmaaldrich.com/nmr
[43]. Fulmer, G. R.; Miller, A. J. M.; Sherden, N. H.; Gottlieb, H. E.; Nudelman, A.; Stoltz, B. M.; Bercaw, J. E.; Goldberg, K. I. Organometallics 2010, 29, 2176-2179.
https://doi.org/10.1021/om100106e
[44]. Allan, J. R.; Barrow, M. J.; Beaumont, P. C.; Macindoe, L. A.; Milburn, G. H. W.; Werninck, A. R. Inorg. Chim. Acta 1988, 148, 85-90.
https://doi.org/10.1016/S0020-1693(00)86015-6
[45]. Sokolov, A. N.; Friscic, T.; Blais, S.; Ripmeester, J. A.; Macgillivray, L. R. Cryst. Growth Des. 2006, 6, 2427-2428.
https://doi.org/10.1021/cg0605133
[46]. Patil, R. S.; Mossine, A. V.; Kumari, H.; Barnes, C. L.; Atwood, J. L. Cryst. Growth Des. 2014, 14, 5212-5218.
https://doi.org/10.1021/cg501014c
[47]. Patil, R. S.; Kumari, H.; Barnes, C. L.; Atwood, J. L. Chem. Commun, 2015, 51, 2304-2307.
https://doi.org/10.1039/C4CC08388A
[48]. Tomura, M.; Yamashita, Y. Chem. Lett. 2001, 6, 532-533.
https://doi.org/10.1246/cl.2001.532
[49]. Bosch, E.; Kruse, S. J.; Groeneman, R. H.; Cryst. Eng. Comm. 2019, 21, 990-993.
https://doi.org/10.1039/C8CE01984C
[50]. Bosch, E. J. Chem. Crystallogr. 2014, 44, 287-292.
https://doi.org/10.1007/s10870-014-0510-x
[51]. Hutchins, K. M.; Unruh, D. K.; Carpenter, D. D.; Groeneman, R. H. Cryst. Eng. Comm. 2018, 20, 7223-7402.
https://doi.org/10.1039/C8CE01090K
[52]. Hutchins, K. M.; Unruh, D. K.; Verdu, F. A.; Groeneman, R. H. Cryst. Growth. Des. 2018, 18, 566-570.
https://doi.org/10.1021/acs.cgd.7b01386
[53]. Bosch, E.; Bowling, N. P.; Darko, J. Cryst. Growth. Des. 2015, 15, 1634-1641.
https://doi.org/10.1021/cg5014076
[54]. Hutchins, K. M.; Dutta, S.; Loren, B. P.; Macgillivray, L. R. Chem. Mater. 2014, 26, 3042-3044.
https://doi.org/10.1021/cm500823t
[55]. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G. J. Chem. Soc. Perkin Trans. II 1987, 12, S1-S19.
https://doi.org/10.1039/p298700000s1
[56]. Mishra, B. K.; Sathyamurthy, N. J. Phys. Chem. A 2005, 109, 6-8.
https://doi.org/10.1021/jp045218c
[57]. Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
https://doi.org/10.1021/j100785a001
[58]. Batsanov, S. S. Inorg. Mater. 2001, 37, 871-885.
https://doi.org/10.1023/A:1011625728803
[59]. Kirchner, M. T.; Boese, R.; Gehrke, A.; Blaser, D. Cryst. Eng. Comm. 2004, 6, 360-366.
https://doi.org/10.1039/B410636A
[60]. Ohkita, M.; Suzuki, T.; Nakatani, K.; Tsuji, T. Chem. Lett. 2001, 30(10), 988-989.
https://doi.org/10.1246/cl.2001.988
[61]. Shivakumar, K.; Vidyasagar, A.; Naidu, A.; Gonnade, R. G. Sureshan, K. M. Cryst. Eng. Comm. 2012, 14, 519-524.
https://doi.org/10.1039/C1CE05997A
Natural Sciences and Engineering Research Council of Canada, University of Lethbridge, Canada, Lagos State University, Nigeria.
Most read articles by the same author(s)
- Ibukun Oluwaseun Shotonwa, Rene T. Boere, Crystallographic identification of a novel 2,4,5-tri(N-methyl-4-pyridinium)-1,3-thiazole with a complex network of polyiodide/iodine counter ions and co-crystallized cyclododecasulfur (S12) , European Journal of Chemistry: Vol. 12 No. 2 (2021): June 2021
- Ibukun Oluwaseun Shotonwa, Rene Theodoor Boere, Crystal and molecular structure of Michler’s ketone as a pure phase , European Journal of Chemistry: Vol. 13 No. 4 (2022): December 2022
- Ibukun Oluwaseun Shotonwa, Adebayo Ponle Oduwole, Oluwapelumi Martin Agosu, Abosede Funke Yusuf, Simeon Okechukwu Eze, Single and mixed dithiocarbamato metal(III) complexes (Co, Rh, and Ir): Crystal and molecular structure description and interplay , European Journal of Chemistry: Vol. 15 No. 3 (2024): September 2024
Smart CitationsSee how this article has been cited at scite.ai
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Downloads
Metrics
License Terms
Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).