Nitro Derivatives of Benzoazacrown Ethers: Synthesis, Structure, and Complexation with Metal and Ammonium Cations and Fluoride Anion

Svetlana N. Dmitrieva,^a Nikolay A. Kurchavov,^a Lyudmila G. Kuz’mina,^b Artem I. Vedernikov,^a Marina V. Churakova,^a Sergey K. Sazonov,^a Judith A. K. Howard,^cand Sergey P. Gromov^a,d@

^aPhotochemistry Center of RAS, FSRC “Crystallography and Photonics”, Russian Academy of Sciences, 119421 Moscow, Russian Federation

^bN.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation

^cChemistry Department, Durham University, DH1 3LE Durham, UK

^dDepartment of Chemistry, M.V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation

^@Corresponding author E-mail: spgromov@mail.ru

DOI: 10.6060/mhc181218g

Macroheterocycles 2019 12(1) 82-93

A method was developed for the synthesis of nitrobenzoazacrown ethers by N-demethylation of N-methyl-nitrobenzoazacrown ethers on treatment with ammonium iodide, resulting in the formation of benzoazacrown ethers in 95–100 % yields. The spatial structure of nitrobenzoazacrown ethers and their complexation behaviour towards alkali and alkaline-earth metal cations, ammonium ions, and fluoride anions were investigated using X-ray diffraction and ¹H NMR spectroscopy. It was shown that the stability of host–guest type complexes of nitrobenzoazacrown ethers with metal and ammonium cations in MeCN-d₃ is lower than the stability of complexes formed by N-alkyl-substituted analogues with the same macrocycle size. It was shown that fluoride anions in DMSO-d₆ or MeCN-d₃ can bind to nitrobenzoazacrown ethers via hydrogen bonding with the NH group of the macrocycle.

References:

Click here to expand or collapse this section

1. (a) Löhr H.-G., Vögtle F. Acc. Chem. Res. 1985, 18, 65–72.
https://doi.org/10.1021/ar00111a001
(b) de Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., McCoy C.P., Rademacher J.T., Rice T.E. Chem. Rev. 1997, 97, 1515–1566.
https://doi.org/10.1021/cr960386p
(c) Valeur B., Leray I. Coord. Chem. Rev. 2000, 205, 3–40.
https://doi.org/10.1016/S0010-8545(00)00246-0
(d) Gokel G.W., Leevy W.M., Weber M.E. Chem. Rev. 2004, 104, 2723–2750.
https://doi.org/10.1021/cr020080k
(e) Ushakov E.N., Alfimov M.V., Gromov S.P. Russ. Chem. Rev. 2008, 77, 39–58.
https://doi.org/10.1070/RC2008v077n01ABEH003757
(f) Gromov S.P. Russ. Chem. Bull. 2008, 57, 1325–1350.
https://doi.org/10.1007/s11172-008-0174-9

2. (a) Izatt R.M., Pawlak K., Bradshaw J.S., Bruening R.L. Chem. Rev. 1991, 91, 1721–2085.
https://doi.org/10.1021/cr00008a003
(b) Rurack K., Resch-Genger U. Chem. Soc. Rev. 2002, 31, 116–127.
https://doi.org/10.1039/b100604p
(c) Fery-Forgues S., Al-Ali F. J. Photochem. Photobiol. C: Photochem. Rev. 2004, 5, 139–153.
https://doi.org/10.1016/j.jphotochemrev.2004.07.001
(d) Ushakov E.N., Gromov S.P., Fedorova O.A., Alfimov M.V. Russ. Chem. Bull. 1997, 46, 463–471.
https://doi.org/10.1007/BF02495396

3. (a) Krakowiak K.E., Bradshaw J.S., Zamecka-Krakowiak D.J. Chem. Rev. 1989, 89, 929–972.
https://doi.org/10.1021/cr00094a008
(b) Bradshaw J.S., Krakowiak K.E., Izatt R.M. Aza-crown macrocycles. In: The Chemistry of Heterocyclic Compounds (Taylor E.C., Ed.) New York: John Wiley&Sons, 1993, 51, 1–885.

4. (a) Gromov S.P., Dmitrieva S.N., Churakova M.V. Russ. Chem. Rev. 2005, 74, 461–488.
https://doi.org/10.1070/RC2005v074n05ABEH001163
(b) DmitrievaS.N., VedernikovA.I., UshakovE.N., Kuz'minaL.G., GromovS.P. Russ. Chem. Bull. 2015, 64, 1726–1745.
https://doi.org/10.1007/s11172-015-1068-2
(c) GromovS.P., DmitrievaS.N., VedernikovA.I., Kuz'minaL.G., ChurakovA.V., StrelenkoY.A., HowardJ.A.K. Eur. J. Org. Chem. 2003, 3189–3199.
https://doi.org/10.1002/ejoc.200300179
(d) Gromov S.P., Dmitrieva S.N., Churakova M.V. Synthesis 2003, 593–597.
https://doi.org/10.1055/s-2003-37662
(e) GromovS.P., DmitrievaS.N., ChurakovaM.V., VedernikovA.I., KurchavovN.A., Kuz'minaL.G., KataevaN.A., HowardJ.A.K. Russ. J. Org. Chem. 2004, 40, 1200–1209.
https://doi.org/10.1023/B:RUJO.0000045906.15567.18
(f) GromovS.P., DmitrievaS.N., VedernikovA.I., KurchavovN.A., Kuz'minaL.G., StrelenkoY.A., AlfimovM.V., HowardJ.A.K. J. Phys. Org. Chem. 2009, 22, 823–833.
https://doi.org/10.1002/poc.1527
(g) DmitrievaS.N., ChurakovaM.V., KurchavovN.A., VedernikovA.I., Kuz'minaL.G., FreidzonA.Y., Bagatur'yantsA.A., StrelenkoY.A., HowardJ.A.K., GromovS.P. Russ. Chem. Bull. 2010, 59, 1192–1206.
https://doi.org/10.1007/s11172-010-0222-0
(h) DmitrievaS.N., ChurakovaM.V., KurchavovN.A., VedernikovA.I., FreidzonA.Y., BasokS.S., Bagatur'yantsA.A., StrelenkoY.A., GromovS.P. Russ. J. Org. Chem. 2011, 47, 1101–1114.
https://doi.org/10.1134/S1070428011070220

5. (a) Gromov S.P., Dmitrieva S.N., Vedernikov A.I., Kurchavov N.A., Kuz'mina L.G., Sazonov S.K., Strelenko Y.A., Alfimov M.V., Howard J.A.K., Ushakov E.N. J. Org. Chem. 2013, 78, 9834–9847.
https://doi.org/10.1021/jo401555a
(b) Gromov S.P., Vedernikov A.I., Lobova N.A., Kuz'mina L.G., Dmitrieva S.N., Strelenko Y.A., Howard J.A.K. J. Org. Chem. 2014, 79, 11416–11430.
https://doi.org/10.1021/jo5018074
(c) Ushakov E.N., Vedernikov A.I., Lobova N.A., Dmitrieva S.N., Kuz'mina L.G., Moiseeva A.A., Howard J.A.K., Alfimov M.V., Gromov S.P. J. Phys. Chem. A. 2015, 119, 13025–13037.
https://doi.org/10.1021/acs.jpca.5b10758

6. Dmitrieva S.N., Churakova M.V., Vedernikov A.I., Kuz'mina L.G., Gromov S.P. Tetrahedron 2011, 67, 2530–2535.
https://doi.org/10.1016/j.tet.2011.02.038

7. Strohmeier G.A., Fabian W.M.F., Uray G. Helv. Chim. Acta 2004, 87, 215–226.
https://doi.org/10.1002/hlca.200490009

8. Frassineti C., Ghelli S., Gans P., Sabatini A., Moruzzi M.S., Vacca A. Anal. Biochem. 1995, 231, 374–382.
https://doi.org/10.1006/abio.1995.9984

9. SAINT, Version 6.02A, Bruker AXS Inc., Madison, Wisconsin (USA), 2001.

10. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H. J. Appl. Crystallogr. 2009, 42, 339–341.
https://doi.org/10.1107/S0021889808042726

11. Sheldrick G.M. Acta Crystallogr. Sect. C. 2015, C71, 3–8.
https://doi.org/10.1107/S2053229614024218

12. Sheldrick G.M. Acta Crystallogr. Sect. A. 2008, A64, 112–122.
https://doi.org/10.1107/S0108767307043930

13. Roberts R.M., Vogt P.J. J. Am. Chem. Soc. 1956, 78, 4778–4782.
https://doi.org/10.1021/ja01599a063

Attachment	Size
mhc181218g_supp.pdf	2.1 MB
mhc181218g.pdf	1.57 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Nitro Derivatives of Benzoazacrown Ethers: Synthesis, Structure, and Complexation with Metal and Ammonium Cations and Fluoride Anion

References: