Multiple Noncovalent Binding in the Intermediates and Products of the Reaction of N,N-Dimethylformamide with Bromine

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

Reaction of nonionic N,N-dimethylformamide (DMF) with bromine under controllable conditions leads to a number of ionic compounds, mainly to bis(N,N-dimethylformamide)hydrogen dibromobromate. Computations with DFT (ωB97xV/dgdzvp) were made for geometry, thermochemistry and electron configuration of products and supposed intermediates. Two labile particles [bis(N,N-dimethylformamide)hydrogen cation and dibromobromate-anion] form stable highly conductive ionic liquid that can be distilled in vacuo without losses or decomposition. A number of molecular complexes of DMF with bromine and water presumed to be intermediates of this reaction. It is a set of halogen and hydrogen bonding that provide an intramolecular binding in these complexes.

Full Text

Restricted Access

About the authors

O. M. Zarechnaya

L. M. Litvinenko Institute of Physical Organic and Coal Chemistry

Email: v_mikhailov@yahoo.com
Russian Federation, Donetsk

V. A. Mikhailov

L. M. Litvinenko Institute of Physical Organic and Coal Chemistry

Author for correspondence.
Email: v_mikhailov@yahoo.com
ORCID iD: 0000-0002-4184-1805
Russian Federation, Donetsk

References

  1. Izutsu K. Electrochemistry in Nonaqueous Solutions. Weinheim: Wiley-VCH, 2010. P. 18.
  2. Rudd E.J., Finkelstein M., Ross S.D. // J. Org. Chem. 1972. Vol. 37. P. 1763. doi: 10.1021/jo00976a021
  3. Schultz G., Hargittai I. // J. Phys. Chem. 1993. Vol. 97. P. 4966. doi: 10.1021/j100121a018
  4. Katayama M., Komori K., Ozutsumi K., Ohtaki H. // Z. Phys. Chem. 2009. Vol. 218. P. 659. doi: 10.1524/zpch.218.6.659.33452
  5. Ratajczyk P., Sobczak S., Katrusiak A. // Cryst. Growth Des. 2019. Vol. 19. P. 896. doi: 10.1021/acs.cgd.8b01452
  6. Shastri A., Das A.K., Krishnakumar S., Singh P.J., Raja Sekhar B.N. // J. Chem. Phys. 2017. Vol. 147. art. 224305. doi: 10.1063/1.5006126
  7. Sałdyka M., Mielke Z., Haupa K. // Spectrochim. Acta (A). 2018. Vol. 190. P. 423. doi: 10.1016/j.saa.2017.09.046
  8. Basma N., Cullen P.L., Clancy A.J., Shaffer M.S.P., Skipper N.T., Headen T.F., Howard C.A. // Mol. Phys. 2019. Vol. 117. P. 3353. doi: 10.1080/00268976.2019.1649494
  9. Hunter E.P.L., Lias S.G. // J. Phys. Chem. Ref. Data. 1998. Vol. 27. P. 413. doi: 10.1063/1.556018
  10. Meot-Ner M. // J. Am. Chem. Soс. 1984. Vol. 106. P. 278. doi: 10.1021/ja00314a003
  11. Adelman R.L. // J. Org. Chem. 1964. Vol. 29. P. 1837. doi: 10.1021/jo01030a041
  12. Cilense M.F., Benedetti A.V., Vollet D.R. // Thermochim. Acta. 1983. Vol. 63. P. 151. doi: 10.1016/0040-6031(83)80080-X
  13. Kuhn S.J., McIntyre J.S. // Can. J. Chem. 1965. Vol. 43. P. 995. doi: 10.1139/v65-134
  14. Tsubomura H., Lang R.P. // J. Am. Chem. Soc. 1961. Vol. 83. P. 2085. doi: 10.1021/ja01470a013
  15. Laurence C., Graton J., Berthelot M., El-Ghomari M.J. // Chem. Eur. J. 2011. Vol. 17. P. 10431. doi: 10.1002/chem.201101071
  16. Guiheneuf G., Abboud J.-L.M., Lachkar A. // Can. J. Chem. 1988. Vol. 66. P. 1032. doi: 10.1139/v88-171
  17. Matsui Y., Date Y. // Bull. Chem. Soc. Japan. 1970. Vol. 43. P. 2828. doi: 10.1246/bcsj.43.2828
  18. Yao Y., Zhao K., Zhuang Y., Chen X., Lu Y., Liu Y. // Chem. Open. 2022. Vol. 11. e202100301. doi: 10.1002/open.202100301
  19. Orefice M., Eldosouky A., Škulj I., Binnemans K. // RSC Adv. 2019. Vol. 9. P. 14910. doi: 10.1039/C9RA01696A
  20. Михайлов В.А. // Укр. хим. ж. 1990. Vol. 56. P. 765.
  21. Bader R.F.W. // J. Phys. Chem. (A). 1998. Vol. 102. P. 7314. doi: 10.1021/jp981794v
  22. Espinosa E., Alkorta I., Elguero J., Molins E. // J. Chem. Phys. 2002. Vol. 117. P. 5529. doi: 10.1063/1.1501133
  23. Boto R.A., Contreras-García J., Tierny J., Piquemal J.-P. // Mol. Phys. 2015. P. 1. doi: 10.1080/00268976.2015.1123777
  24. Politzer P., Murray J. In: Chemical Reactivity in Confined Systems / Eds P.K. Chattaraj, D. Chakraborty. Wiley, 2021. P. 113. doi: 10.1002/9781119683353.ch7
  25. Becke A.D., Edgecombe K.E. // J. Chem. Phys. 1990. Vol. 92. P. 5397. doi: 10.1063/1.458517
  26. Schmider H.L., Becke A.D. // J. Mol. Struct. 2000. Vol. 527. P. 51. doi: 10.1016/S0166-1280(00)00477-2
  27. Koch U., Popelier P.L.A. // J. Phys. Chem. 1995. Vol. 99. P. 9747. doi: 10.1021/j100024a016
  28. Mata I., Alkorta I., Espinosa E., Molins E. // Chem. Phys. Lett. 2011. Vol. 507. P. 185. doi: 10.1016/j.cplett.2011.03.055
  29. Matta C.F., Hernández-Trujillo J., Tang T., Bader R.F.W. // Chem. Eur. J. 2003. Vol. 9. P. 1940. doi: 10.1002/chem.200204626
  30. Della Porta P., Zanasi R., Monaco G. // J. Comput. Chem. 2015. Vol. 36. P. 707. doi: 10.1002/jcc.23841
  31. Silvi B., Alikhani M.E., Ratajchak H. // J. Mol. Model. 2020. Vol. 26. art.62. doi: 10.1007/s00894-019-4283-1
  32. Alkorta I., Silva A.F., Popelier P.L.A. // Molecules. 2020. Vol. 25. art. 2674. doi: 10.3390/molecules25112674
  33. Kazama H., Tsushima S., Takao K. // Cryst. Growth Des. 2019. Vol. 19. P. 6048. doi: 10.1021/acs.cgd.9b01214
  34. Дорохова Т.В., Михайлов В.А., Каниболоцкий А.Л., Прокопьева Т.М., Савелова В.А., Попов А.Ф. // ТЭХ. 2008. Т. 44. С. 298; Dorokhova T.V., Mikhailov V.A., Kanibolotskii A.L., Prokop’eva T.M., Savelova V.A., Popov A.F. // Theor. Exp. Chem. 2008, Vol. 44. P. 307. doi: 10.1007/s11237-008-9042-9
  35. Ruasse M.-F., Aubard J., Galland B., Adenier A. // J. Phys. Chem. 1986. Vol. 90. P. 4382. doi: 10.1021/j100409a034
  36. Zundel G. // Angew. Chem. Int. Ed. 1969. Vol. 8. P. 499. doi: 10.1002/anie.196904991
  37. Fuoss R.M., Kraus C.A. // J. Am. Chem. Soc. 1933. Vol. 55. P. 476. doi: 10.1021/ja01329a006
  38. Agmon N., Bakker H.J., Campen R.K., Henchman R.H., Pohl P., Roke S., Thamer M., Hassanali A. // Chem. Rev. 2016. Vol. 116. P. 7642. doi: 10.1021/acs.chemrev.5b00736
  39. Haller H., Ellwanger M., Higelin A., Riedel S. // Angew. Chem. Int. Ed. 2011. Vol. 50. P. 11528. doi: 10.1002/anie.201105237
  40. Gully T.A., Voßnacker P., Schmid J.R., Beckers H., Riedel S. // ChemistryOpen. 2021. Vol. 10. P. 255. doi: 10.1002/open.202000263
  41. Yuan W., Yang X., He L., Xue Y., Qin S., Tao G. // Front. Chem. 2018. Vol. 6. Art. 59. doi: 10.3389/fchem.2018.00059
  42. Perkins C.W., Martin J.C., Arduengo A.J., Lau W., Alegria A., Kochi J.K. // J. Am. Chem. Soc. 1980. Vol. 102. P. 7753. doi: 10.1021/ja00546a019
  43. Ivlev S.I., Gaul K., Chen M., Karttunen A.J., Berger R., Kraus F. // Chem. Eur. J. 2019. Vol. 25. P. 5793. doi: 10.1002/chem.201900442
  44. Alder R.W., Blake M.E., Bufali S., Butts C.P., Orpen A.G., Schütz J., Williams S.J. // J. Chem. Soc. Perkin Trans. 1. 2001. Vol. 14. P. 1586. doi: 10.1039/B104110J
  45. Wlodarczyk J.K., Küttinger M., Friedrich A.K., Schumacher J.O. // J. Power Sources. 2021. Vol. 508, art. 230202. doi: 10.1016/j.jpowsour.2021.230202
  46. Xu Y., Xie C., Li X. // Trans. Tianjin Univ. 2022. Vol. 28. P. 186. doi: 10.1007/s12209-022-00327-w
  47. Huber K.P., Herzberg G. Molecular Spectra and Molecular Structure. IV. Constants of Diatomic Molecules. New York: Van Nostrand Reinhold Co., 1979.
  48. Powell B.M., Heal K.M., Torrie B.H. // Mol. Phys. 1984. Vol. 53. P. 929. doi: 10.1080/00268978400102741
  49. Császár A.G., Czakó G., Furtenbacher T., Tennyson J., SzalayV., Shirin S.V., Zobov N.F., Polyansky O.L. // J. Chem. Phys. 2005. Vol. 122. Art. no. 214305. doi: 10.1063/1.1924506
  50. Graner G., Rossetti C., Bailly D. // Mol. Phys. 1986. Vol. 58. P. 627. doi: 10.1080/00268978600101431
  51. Nemec V., Fotović L., Vitasović T., Cinčić D. // CrystEngComm. 2019. Vol. 21. P. 3251. doi: 10.1039/C9CE00340A
  52. Jones R.H., Knight K.S., Marshall W.G., Coles S.J., Horton P.N., Pitak M.B. // CrystEngComm. 2013. Vol. 15. P. 8572. doi: 10.1039/C3CE41472H
  53. Suponitsky K.Yu., Burakov N.I., Кanibolotsky A.L., Mikhailov V.A. // J. Phys. Chem. (A). 2016. Vol. 120. P. 4179. doi: 10.1021/acs.jpca.6b02192
  54. Zarechnaya O.M., Anisimov A.A., Belov E.Yu., Burakov N.I., Kanibolotsky A.L., Mikhailov V.A. // RSC Adv. 2021. Vol. 11. P. 6131. doi: 10.1039/D0RA08165E
  55. Saunders L.K., Pallipurath A.R., Gutmann M.J., Nowell H., Zhang N., Allan D.R. // CrystEngComm. 2021. Vol. 23. P. 6180. doi: 10.1039/D1CE00355K
  56. Pichierri F. // Chem. Phys. Lett. 2011. Vol. 515. P. 116. doi: 10.1016/j.cplett.2011.09.003
  57. Boer F.P. // J. Am. Chem. Soc. 1966. Vol. 88. P. 1572. doi: 10.1021/ja00959a059
  58. Hussain M.S., Schlemper E.O. // J. Chem. Soc. Dalton Trans. 1980. Vol. 35. P. 750. doi: 10.1039/DT9800000750
  59. Stuart D., Wetmore S.D., Gerken M. // Angew. Chem. 2017. Vol. 129. P. 16598. doi: 10.1002/ange.201710263
  60. Allen F.H., Watson D.G., Brammer L., Orpen A.G., Taylor R. // Int. Tables Cryst. 2006. Vol. C. P. 790. doi: 10.1107/97809553602060000621
  61. Molčanov K., Jelsch C., Wenger E., Stare J., Madsen A.Ø., Kojić-Prodić B. // CrystEngComm. 2017. Vol. 19. P. 3898. doi: 10.1039/C7CE00501F
  62. Keil H., Sonnenberg K., Muller C., Herbst-Irmer R., Beckers H., Riedel S., Stalke D. // Angew. Chem. Int. Ed. 2021. Vol. 60. P. 2569. doi: 10.1002/anie.202013727
  63. Sonnenberg K., Mann L., Redeker F.A., Schmidt B., Riedel S. // Angew. Chem. Int. Ed. 2020. Vol. 59. P. 5464. doi: 10.1002/anie.201903197.
  64. Nizzi K. E., Pommerenning C.A., Sunderlin L. // J. Phys. Chem. (A). 1998. Vol. 102. P. 7674. doi: 10.1021/JP9824508
  65. Christe K.O., Bau R., Zhao D. // Z. anorg. allg. Chem. 1991. Vol. 593. P. 46. doi: 10.1002/Zaac.19915930106
  66. Wang H., Liu H., Wang M., Huang M., Shi X., Wang T., Cong X., Yan J., Wu J.// Iscience. 2021. Vol. 24. N. 6. Art. 102693. doi: 10.1016/j.isci.2021.102693
  67. Saikia I., Borah A.J., Phukan P. // Chem. Rev. 2016. Vol. 116. P. 6837. doi: 10.1021/acs.chemrev.5b00400
  68. Beato E.P., Mazzarella D., Balletti M., Melchiorre P. // Chem. Sci. 2020. Vol. 11. P. 6312. doi: 10.1039/D0SC02313B
  69. Talukdar R. // Org. Biomol. Chem. 2020. Vol. 18. P. 8294. doi: 10.1039/D0OB01652G
  70. Mayer J.M. // J. Am. Chem. Soc. 2023. Vol. 145. P. 7050. doi.org/10.1021/jacs.2c10212
  71. Lowry T.H., Richardson K.S. Mechanism and Theory in Organic Chemistry. HarperCollins, 1987. P. 425.
  72. Zabolotniy A.A., Trush E.N., Zarechnaya O.M., Mikhailov V.A. // J. Ionic Liq. 2022. Vol. 2. Art. 100045. doi: 10.1016/j.jil.2022.100045
  73. Juillard J. In: Recommended Methods for Purification of Solvents and Tests for Impurities / Ed. J.F. Coetzee. Pergamon, 1982.
  74. Neese F., Wennmohs F., Becker U., Riplinger C. // J. Chem. Phys. 2020. Vol. 152. Art. 224108. doi: 10.1063/5.0004608
  75. Godbout N., Salahub D.R., Andzelm, J., Wimmer E. // Can. J. Chem. 1992. Vol. 70. P. 560. doi: 10.1139/v92-079
  76. Mardirossian N., Head-Gordon M. // Phys. Chem. Chem. Phys. 2014. Vol. 16. P. 9904. doi: 10.1039/C3CP54374A
  77. Vydrov O.A., Van Voorhis T. // J. Chem. Phys. 2010. Vol. 133. Art. 244103. doi: 10.1063/1.3521275.
  78. Pritchard B.P., Altarawy D., Didier B.T., Gibson T.D., Windus T.L. // J. Chem. Inf. Model. 2019. Vol. 59. P. 4814. doi: 10.1021/acs.jcim.9b00725; www.basissetexchange.org
  79. Goerigk L., Hansen A., Bauer C., Ehrlich S., Najibi A., Grimme S. // Phys. Chem. Chem. Phys. 2017. Vol. 19. P. 32184. doi: 10.1039/C7CP04913G
  80. Goerigk L., Mehta N. // Aus. J. Chem. 2019. Vol. 72. P. 563. doi: 10.1071/CH19023
  81. Lu T., Chen F. // J. Comput. Chem. 2012. Vol. 33. P. 580. doi: 10.1002/jcc.22885
  82. Zhang J., Lu T. // Phys. Chem. Chem. Phys. 2021. Vol. 23. P. 20323. doi: 10.1039/D1CP02805G
  83. Lu T. // J. Mol. Model. 2021. Vol. 27. P. 263. doi: 10.1007/s00894-021-04884-0
  84. Humphrey W., Dalke A., Schulten K. // J. Mol. Graphics. 1996. Vol. 14. P. 33. doi: 10.1016/0263-7855(96)00018-5
  85. Macrae C.F., Sovago I., Cottrell S.J., Galek P.T.A., McCabe P., Pidcock E., Platings M., Shields G.P., Stevens J.S., Towler M., Wood P.A. // J. Appl. Cryst. 2020. Vol. 53. P. 226. doi: 10.1107/S1600576719014092

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Scheme 1

Download (95KB)
Indexing metadata
3. Fig. 1. Binary complexes of DMFA with bromine

Download (129KB)
Indexing metadata
4. Fig. 2. Triple complexes of DMFA with bromine of stoichiometry 1:2 and 2:1

Download (125KB)
Indexing metadata
5. Fig. 3. Binary complexes of DMFA with hydrogen bromide

Download (139KB)
Indexing metadata
6. Fig. 4. Complexes of DMFA with water

Download (134KB)
Indexing metadata
7. Fig. 5. Mixed-ligand ternary complexes of DMFA with water and bromine

Download (372KB)
Indexing metadata
8. Fig. 6. General view of ternary complexes DMFA-Br2-Br-

Download (106KB)
Indexing metadata
9. Fig. 7. General view of the molecule of the putative ionic intermediates XXI-XXIII

Download (199KB)
Indexing metadata
10. Fig. 8. General view of cations as reaction products

Download (228KB)
Indexing metadata
11. Scheme 2

Download (65KB)
Indexing metadata

Copyright (c) 2024 Russian Academy of Sciences

This website uses cookies

You consent to our cookies if you continue to use our website.

About Cookies