25 years of NICS – much more than nothing! Letter to the Editor
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Abstract
The famous aromaticity index NICS (nucleus independent chemical shift) was introduced 25 years ago. The authors use this anniversary for a short and to some degree personal retrospective.
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References
P. von R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van Eikema Hommes, J. Am. Chem. Soc. 118 (1996) 6317 (https://doi.org/10.1021/ja960582d)
H. Jiao, P. von R. Schleyer, Y. Mo, M. A. McAllister, T. T. Tidwell, J. Am. Chem. Soc. 119 (1997) 7075 (https://doi.org/10.1021/ja970380x)
M. Saunders, H. A. Jiménez-Vázquez, R. J. Cross, S. Mroczkowski, D. I. Freedberg, F. A. L. Anet, Nature 367 (1994) 256 (https://doi.org/10.1038/367256a0)
M. Buehl, W. Thiel, H. Jiao, P. v. R. Schleyer, M. Saunders, F. A. L. Anet, J. Am. Chem. Soc. 116 (1994) 6005 (https://doi.org/10.1021/ja00092a076)
M. Bühl, A. Hirsch, Chem. Rev. 101 (2001) 1153 (https://doi.org/10.1021/cr990332q)
E. Shabtai, A. Weitz, R. C. Haddon, R. E. Hoffman, M. Rabinovitz, A. Khong, R. J. Cross, M. Saunders, P.-C. Cheng, L. T. Scott, J. Am. Chem. Soc. 120 (1998) 6389 (https://doi.org/10.1021/ja9805831)
Web of Science online database, https://www.webofscience.com
Z. Chen, C. S. Wannere, C. Corminboeuf, R. Puchta, P. von R. Schleyer, Chem. Rev. 105 (2005) 3842 (https://doi.org/10.1021/cr030088+)
P. v. R. Schleyer, H. Jiao, H. M. Sulzbach, H. F. Schaefer, J. Am. Chem. Soc. 118 (1996) 2093 (https://doi.org/10.1021/ja953126i)
D. Moran, F. Stahl, H. F. Bettinger, H. F. Schaefer, P. v. R. Schleyer, J. Am. Chem. Soc. 125 (2003) 6746 (https://doi.org/10.1021/ja034497z)
S. Klod, E. Kleinpeter, J. Chem. Soc., Perkin Trans. 2 (2001) 1893 (https://doi.org/10.1039/B009809O)
S. Klod, A. Koch, E. Kleinpeter, J. Chem. Soc., Perkin Trans. 2 (2002) 1506 (https://doi.org/10.1039/B204629F)
E. Kleinpeter, S. Klod, J. Mol. Struct. 704 (2004) 79 (https://doi.org/https://doi.org/10.1016/j.molstruc.2003.12.062)
E. F. Kleinpeter, A. Koch, ARKIVOC 2012 (2011) 94 (https://doi.org/10.3998/ark.5550190.0013.510)
A. Stanger, J. Org. Chem. 71 (2006) 883 (https://doi.org/10.1021/jo051746o)
J. Pipek, P. G. Mezey, J. Chem. Phys. 90 (1989) 4916 (https://doi.org/10.1063/1.456588)
P. von R. Schleyer, H. Jiao, N. J. R. van E. Hommes, V. G. Malkin, O. L. Malkina, J. Am. Chem. Soc. 119 (1997) 12669 (https://doi.org/10.1021/ja9719135)
P. von R. Schleyer, M. Manoharan, Z.-X. Wang, B. Kiran, H. Jiao, R. Puchta, N. J. R. van Eikema Hommes, Org. Lett. 3 (2001) 2465 (https://doi.org/10.1021/ol016217v)
C. Corminboeuf, T. Heine, J. Weber, Phys. Chem. Chem. Phys. 5 (2003) 246 (https://doi.org/10.1039/B209674A)
T. Heine, P. v. R. Schleyer, C. Corminboeuf, G. Seifert, R. Reviakine, J. Weber, J. Phys. Chem., A 107 (2003) 6470 (https://doi.org/10.1021/jp035163z)
J. A. Bohmann, F. Weinhold, T. C. Farrar, J. Chem. Phys. 107 (1997) 1173 (https://doi.org/10.1063/1.474464)
M. Baranac-Stojanović, J. Org. Chem. 85 (2020) 4289 (https://doi.org/10.1021/acs.joc.9b03472)
M. Mauksch, S. B. Tsogoeva, Chem. – A Eur. J. 27 (2021) 14660 (https://doi.org/https://doi.org/10.1002/chem.202102230)
M. Jirásek, H. L. Anderson, M. D. Peeks, Acc. Chem. Res. 54 (2021) 3241 (https://doi.org/10.1021/acs.accounts.1c00323)
G. J. Richards, J. P. Hill, Acc. Chem. Res. 54 (2021) 3228 (https://doi.org/10.1021/acs.accounts.1c00315)
J. I. Wu, F. G. Pühlhofer, P. von R. Schleyer, R. Puchta, B. Kiran, M. Mauksch, N. J. R. van E. Hommes, I. Alkorta, J. Elguero, J. Phys. Chem., A 113 (2009) 6789 (https://doi.org/10.1021/jp902983r)
S. Radenković, J. Đurđević, P. Bultinck, Phys. Chem. Chem. Phys. 14 (2012) 14067 (https://doi.org/10.1039/C2CP41472D)
S. Radenković, I. Gutman, P. Bultinck, J. Phys. Chem., A 116 (2012) 9421 (https://doi.org/10.1021/jp307281y)
S. Radenković, J. Kojić, J. Petronijević, M. Antić, J. Phys. Chem., A 118 (2014) 11591 (https://doi.org/10.1021/jp507309m)
M. Antić, B. Furtula, S. Radenković, J. Phys. Chem., A 121 (2017) 3616 (https://doi.org/10.1021/acs.jpca.7b02521)
C. Riesinger, G. Balázs, M. Seidl, M. Scheer, Chem. Sci. 12 (2021) 13037 (https://doi.org/10.1039/D1SC04296C)
J. T. Boronski, J. A. Seed, D. Hunger, A. W. Woodward, J. van Slageren, A. J. Wooles, L. S. Natrajan, N. Kaltsoyannis, S. T. Liddle, Nature 598 (2021) 72 (https://doi.org/10.1038/s41586-021-03888-3)
S. Radenković, M. Antić, N. D. Savić, B. Đ. Glišić, New J. Chem. 41 (2017) 12407 (https://doi.org/10.1039/C7NJ02634J)
M. Walther, R. Puchta, RSC Adv. 2 (2012) 5815 (https://doi.org/10.1039/C2RA20665J)
R. Puchta, B. Neumüller, K. Dehnicke, Zeitschr. Anorg. Allg. Chem. 635 (2009) 1196 (https://doi.org/https://doi.org/10.1002/zaac.200801360)
A. I. Boldyrev, L.-S. Wang, Chem. Rev. 105 (2005) 3716 (https://doi.org/10.1021/cr030091t)
S. Radenković, P. Bultinck, J. Phys. Chem., A 115 (2011) 12493 (https://doi.org/10.1021/jp2020947)
S. Đorđević, S. Radenković, Phys. Chem. Chem. Phys. 21 (2019) 7105 (https://doi.org/10.1039/c9cp00541b)
M. M. Hossain, M. S. Mirzaei, S. V Lindeman, S. Mirzaei, R. Rathore, Org. Chem. Front. 8 (2021) 2393 (https://doi.org/10.1039/D1QO00068C)
K. Amsharov, D. I. Sharapa, O. A. Vasilyev, M. Oliver, F. Hauke, A. Goerling, H. Soni, A. Hirsch, Carbon N. Y. 158 (2020) 435 (https://doi.org/https://doi.org/10.1016/j.carbon.2019.11.008)
Z. Chen, J. I. Wu, C. Corminboeuf, J. Bohmann, X. Lu, A. Hirsch, P. von R. Schleyer, Phys. Chem. Chem. Phys. 14 (2012) 14886 (https://doi.org/10.1039/C2CP42146A)
D. Tzeli, I. D. Petsalakis, G. Theodorakopoulos, F.-U. Rahman, Y. Yu, J. Rebek, Phys. Chem. Chem. Phys. 23 (2021) 19647 (https://doi.org/10.1039/D1CP02277F)
Y. Cohen, S. Slovak, L. Avram, Chem. Commun. 57 (2021) 8856 (https://doi.org/10.1039/D1CC02906A)
D. Ćoćić, R. Puchta, R. van Eldik, J. Coord. Chem. 73 (2020) 2602 (https://doi.org/10.1080/00958972.2020.1820494)
R. Puchta, R. van Eldik, Eur. J. Inorg. Chem. 2007 (2007) 1120 (https://doi.org/https://doi.org/10.1002/ejic.200600715)
T. V. Soldatović, E. Selimović, B. Šmit, D. Ašanin, N. S. Planojević, S. D. Marković, R. Puchta, B. M. Alzoubi, J. Coord. Chem. 72 (2019) 690 (https://doi.org/10.1080/00958972.2019.1569229)
S. Jovanović, R. Puchta, O. Klisurić, Ž. D. Bugarčić, J. Coord. Chem. 69 (2016) 735 (https://doi.org/10.1080/00958972.2016.1146257)
B. Petrović, Ž. D. Bugarčić, A. Dees, I. Ivanović-Burmazović, F. W. Heinemann, R. Puchta, S. N. Steinmann, C. Corminboeuf, R. van Eldik, Inorg. Chem. 51 (2012) 1516 (https://doi.org/10.1021/ic201807a)
M. D. Kostić, V. M. Divac, B. M. Alzoubi, R. Puchta, Zeitschr. Naturforsch., B 71 (2016) 883 (https://doi.org/doi:10.1515/znb-2016-0055)
I. Casademont-Reig, R. Guerrero-Avilés, E. Ramos-Cordoba, M. Torrent-Sucarrat, E. Matito, Angew. Chemie Int. Ed. 60 (2021) 24080 (https://doi.org/https://doi.org/10.1002/anie.202108997)
J. Y. M. Chan, Y. Okada, T. Kawata, N. Kobayashi, D. K. P. Ng, Org. Lett. 23 (2021) 5942 (https://doi.org/10.1021/acs.orglett.1c02039).
M. Rauhalahti, D. Sundholm, M. P. Johansson, Phys. Chem. Chem. Phys. 23 (2021) 16629 (https://doi.org/10.1039/D1CP02381K)
H. Kawashima, S. Ukai, R. Nozawa, N. Fukui, G. Fitzsimmons, T. Kowalczyk, H. Fliegl, H. Shinokubo, J. Am. Chem. Soc. 143 (2021) 10676 (https://doi.org/10.1021/jacs.1c04348)
F. Golpayegani, Z. Mirjafary, J. M. Aliabad, H. Saeidian, Comput. Theor. Chem. 1206 (2021) 113469 (https://doi.org/https://doi.org/10.1016/j.comptc.2021.113469)
M. Y. Borzehandani, E. Abdulmalek, M. B. Abdul Rahman, M. A. M. Latif, Polymers (Basel). 13 (2021) (https://doi.org/10.3390/polym13111861)
C. Zeng, W. Shen, X. Xie, M. Li, Polym. Sci., A 52 (2010) 1355 (https://doi.org/10.1134/S0965545X1012014X)
M. Mauksch, S. B. Tsogoeva, ChemPhysChem 17 (2016) 963 (https://doi.org/https://doi.org/10.1002/cphc.201600086)
H. Jiao, P. von Ragué Schleyer, J. Chem. Soc., Perkin Trans. 2 (1994) 407 (https://doi.org/10.1039/P29940000407)
M. Mauksch, V. Gogonea, H. Jiao, P. von R. Schleyer, Angew. Chemie Int. Ed. 37 (1998) 2395 (https://doi.org/https://doi.org/10.1002/(SICI)1521-3773(19980918)37:17<2395::AID-ANIE2395>3.0.CO;2-W)
C. Castro, C. M. Isborn, W. L. Karney, M. Mauksch, P. von R. Schleyer, Org. Lett. 4 (2002) 3431 (https://doi.org/10.1021/ol026610g)
C. Castro, Z. Chen, C. S. Wannere, H. Jiao, W. L. Karney, M. Mauksch, R. Puchta, N. J. R. van E. Hommes, P. von R. Schleyer, J. Am. Chem. Soc. 127 (2005) 2425 (https://doi.org/10.1021/ja0458165)
Z. Huang, Y. Zhang, W.-X. Zhang, J. Wei, S. Ye, Z. Xi, Nat. Commun. 12 (2021) 1319 (https://doi.org/10.1038/s41467-021-21648-9)
K. An, T. Shen, J. Zhu, Organometallics 36 (2017) 3199 (https://doi.org/10.1021/acs.organomet.7b00341)
C. Zhu, S. Li, M. Luo, X. Zhou, Y. Niu, M. Lin, J. Zhu, Z. Cao, X. Lu, T. Wen, Z. Xie, P. v. R. Schleyer, H. Xia, Nat. Chem. 5 (2013) 698 (https://doi.org/10.1038/nchem.1690)
M. Mauksch, S. B. Tsogoeva, Chem. – A Eur. J. 16 (2010) 7843 (https://doi.org/https://doi.org/10.1002/chem.201000396)
M. K. Milčić, B. D. Ostojić, S. D. Zarić, Inorg. Chem. 46 (2007) 7109 (https://doi.org/10.1021/ic062292w)
M. Mauksch, S. B. Tsogoeva, Chem. – A Eur. J. 24 (2018) 10059 (https://doi.org/https://doi.org/10.1002/chem.201802270)
D. W. Szczepanik, M. Solà, ChemistryOpen 8 (2019) 219 (https://doi.org/https://doi.org/10.1002/open.201900014)
I. Fernández, G. Frenking, Chem. – A Eur. J. 13 (2007) 5873 (https://doi.org/https://doi.org/10.1002/chem.200601674)
S. Radenković, S. Đorđević, Phys. Chem. Chem. Phys. 23 (2021) 11240 (https://doi.org/10.1039/D1CP00784J)
J. Đ. Nikolić, S. Đorđević, S. Radenković, J. Mol. Model. 26 (2020) 275 (https://doi.org/10.1007/s00894-020-04543-w)
I. Gutman, S. Radenkovic, M. Antic, J. Djurdjevic, J. Serb. Chem. Soc. 78 (2013) 1539 (https://doi.org/10.2298/JSC130520057G)
S. Radenković, M. Antić, S. Đorđević, B. Braïda, Comput. Theor. Chem. 1116 (2017) (https://doi.org/10.1016/j.comptc.2017.01.028)
S. Jeremić, S. Radenković, M. Filipović, M. Antić, A. Amić, Z. Marković, J. Mol. Graph. Model. 72 (2017) 240 (https://doi.org/https://doi.org/10.1016/j.jmgm.2017.01.011)
P. Lazzeretti, Phys. Chem. Chem. Phys. 6 (2004) 217 (https://doi.org/10.1039/B311178D)
P. von Ragué Schleyer, H. Jiao, B. Goldfuss, P. K. Freeman, Angew. Chemie Int. Ed. English 34 (1995) 337 (https://doi.org/https://doi.org/10.1002/anie.199503371)
L. Nyulászi, P. von R. Schleyer, J. Am. Chem. Soc. 121 (1999) 6872 (https://doi.org/10.1021/ja983113f)
A. Stanger, Eur. J. Org. Chem. 2020 (2020) 3120 (https://doi.org/https://doi.org/10.1002/ejoc.201901829)
R. Gershoni-Poranne, A. Stanger, Chem. Soc. Rev. 44 (2015) 6597 (https://doi.org/10.1039/C5CS00114E)
M. Solà, F. Feixas, J. O. C. Jiménez-Halla, E. Matito, J. Poater, Symmetry 2 (2010) (https://doi.org/10.3390/sym2021156)
M. D. Zermeño-Macías, M. M. González-Chávez, F. Méndez, A. Richaud, R. González-
-Chávez, L. E. Ojeda-Fuentes, P. D. Niño-Moreno, R. Martínez, Mol. 26 (2021) (https://doi.org/10.3390/molecules26165078).