European Journal of Chemistry

Structural diversity in the solid-state architectures of bis(4-pyridyl)acetylene and its derivatives

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Ibukun Oluwaseun Shotonwa
Rene Theodoor Boere

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.


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Shotonwa, I. O.; Boere, R. T. Structural Diversity in the Solid-State Architectures of bis(4-pyridyl)acetylene and Its Derivatives. Eur. J. Chem. 2020, 11, 6-14.

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References

[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

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