Home / Articles / Synthesis and properties of duplicate 6,6'-linkered 1,5-diazabicyclo[3.1.0]hexanes

Synthesis and properties of duplicate 6,6'-linkered 1,5-diazabicyclo[3.1.0]hexanes

Dmitry Victorovich Khakimov 1
Dmitry Victorovich Khakimov
, 
Vladimir Vladimirovich Kuznetsov 1
Vladimir Vladimirovich Kuznetsov
, 
Andrey Sergeevich Dmitrenok 1
Andrey Sergeevich Dmitrenok
, 
Alexander Sergeyevich Goloveshkin 2
Alexander Sergeyevich Goloveshkin
, 
10.71267/mencom.8037
Published 23 September 2026
Communication
0
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Khakimov D. V. et al. Synthesis and properties of duplicate 6,6'-linkered 1,5-diazabicyclo[3.1.0]hexanes // Mendeleev Communications. 2026.
GOST all authors (up to 50)
Copy cite
Khakimov D. V., Kuznetsov V. V., Dmitrenok A. S., Goloveshkin A. S., Samigullina A. I. Synthesis and properties of duplicate 6,6'-linkered 1,5-diazabicyclo[3.1.0]hexanes // Mendeleev Communications. 2026.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.71267/mencom.8037
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.8037
TI - Synthesis and properties of duplicate 6,6'-linkered 1,5-diazabicyclo[3.1.0]hexanes
T2 - Mendeleev Communications
AU - Khakimov, Dmitry Victorovich
AU - Kuznetsov, Vladimir Vladimirovich
AU - Dmitrenok, Andrey Sergeevich
AU - Goloveshkin, Alexander Sergeyevich
AU - Samigullina, Aida Ildusovna
PY - 2026
DA - 2026/09/23
PB - Mendeleev Communications
ER -
BibTex
Cite this
BibTex (up to 50 authors)
Copy cite
@article{2026_Khakimov,
author = {Dmitry Victorovich Khakimov and Vladimir Vladimirovich Kuznetsov and Andrey Sergeevich Dmitrenok and Alexander Sergeyevich Goloveshkin and Aida Ildusovna Samigullina},
title = {Synthesis and properties of duplicate 6,6'-linkered 1,5-diazabicyclo[3.1.0]hexanes},
journal = {Mendeleev Communications},
year = {2026},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.8037},
doi = {10.71267/mencom.8037}
}
Views / Visits
46 / 46

Keywords

1,5-diazabicyclo[3.1.0]hexanes
diaziridines
predictive crystal modeling
synthesis
thermochemical characteristics

Abstract

A series of bi- and bis-1,5-diazabicyclo[3.1.0]hexanes connected by linkers through 6,6' positions were synthesized and characterized, their enthalpies of formation being high ranging within 50–115 kcal mol--1. For cyclohexane dispirotethered diazabicyclohexanes, an experimental density of 1.314 g cm--3 at 120 K was determined, which is one of the highest among related analogs. Model calculations of crystal packings were performed and compared with experimental data.

References

2.
Progress in the chemistry of nitrogen-, oxygen- and sulfur-containing heterocyclic systems
Makhova N.N., Belen’kii L.I., Gazieva G.A., Dalinger I.L., Konstantinova L.S., Kuznetsov V.V., Kravchenko A.N., Krayushkin M.M., Rakitin O.A., Starosotnikov A.M., Fershtat L.L., Shevelev S.A., Shirinian V.Z., Yarovenko V.N.
Russian Chemical Reviews, 2020
4.
Kuznetsov Vladimir Vladimirovich, Kachala Vadim Vadimovich, Makhova Nina Nikolaevna
Mendeleev Communications, 2018
5.
Nitrodiaziridines: Unattainable yet, but Desired Energetic Materials
Khakimov D.V., Fershtat L.L., Pivina T.S., Makhova N.N.
Journal of Physical Chemistry A, 2021
6.
Enthalpy of formation of 6-phenyl-1,5-diazabicyclo[3.1.0]hexane by combustion calorimetry and theoretical approach for efficient prediction of thermochemistry of diaziridines
Lukyanova V.A., Kuznetsov V.V., Konstantinova N.M., Dmitrenok A.S., Kosaya M.P., Dorofeeva O.V., Druzhinina A.I.
Physical Chemistry Chemical Physics, 2023
7.
New Trends in Diaziridine Formation and Transformation (a Review)
Tachrim Z.P., Wang L., Murai Y., Hashimoto M.
Molecules, 2021
8.
Advances in small molecule selective ligands for heteromeric nicotinic acetylcholine receptors
Matera C., Papotto C., Dallanoce C., De Amici M.
Pharmacological Research, 2023
9.
Synthesis and psychotropic activity of functionally substituted diaziridines and bisdiaziridines
Kostyanovskii R.G., Shustov G.V., Nabiev O.G., Denisenko S.N., Sukhanova S.A., Lavretskaya É.F.
Pharmaceutical Chemistry Journal, 1986
11.
Tetramezine metabolism in rats
Prokopov A.A., Kotlova L.I., Berlyand A.S.
Pharmaceutical Chemistry Journal, 2007
14.
Synthesis, structure and peculiarity of conformational behavior of 1,5-diazabicyclo[3.1.0]hexanes
Kuznetsov V.V., Khakimov D.V., Dmitrenok A.S., Goloveshkin A.S.
Journal of Molecular Structure, 2022
15.
Lukyanova Vera Aleksandrovna, Kuznetsov Vladimir Vladimirovich, Konstantinova Natalia M., Dmitrenok Andrey Sergeevich, Kosaya Mariya Petrovna, Dorofeeva Olga Vital'evna, Druzhynina Anna Ivanovna
Mendeleev Communications, 2025
16.
Molecular structure of gaseous 6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane studied by electron diffraction and quantum-chemical calculations
Belyakov A.V., Kuznetsov V.V., Kormil’tsyna N.S., Rykov A.N., Dmitrenok A.S., Tokarev K.L., Shishkov I.F.
Structural Chemistry, 2025
21.
Density functional theory with London dispersion corrections
Grimme S.
Wiley Interdisciplinary Reviews: Computational Molecular Science, 2011
22.
ref-10.71267-mendc7538-1-22-1-0
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, et. al.
2016
23.
A multipole approximation of the electrostatic potential of molecules
Dzyabchenko A.V.
Russian Journal of Physical Chemistry A, 2008
24.
From molecule to solid: The prediction of organic crystal structures
Dzyabchenko A.V.
Russian Journal of Physical Chemistry A, 2008
28.
Computational insight into the crystal structures of cubane and azacubanes
Khakimov D.V., Svitanko I.V., Pivina T.S.
Journal of Molecular Modeling, 2024
30.
Asymmetric nitrogen—41
Shustov G.V., Denisenko S.N., Chervin I.I., Asfandiarov N.L., Kostyanovsky R.G.
Tetrahedron, 1985
31.
Synthesis and Ignition Properties Research of 1,5-Diazabicyclo[3.1.0]Hexane Type Compounds as Potential Green Hypergolic Propellants
Zhang X., Shen L., Luo Y., Jiang R., Sun H., Liu J., Fang T., Fan H., Liu Z.
Industrial & Engineering Chemistry Research, 2017
32.
Molecular structure of 1,5-diazabicyclo[3.1.0]hexane as determined by gas electron diffraction and quantum-chemical calculations
Vishnevskiy Y.V., Vogt N., Vogt J., Rykov A.N., Kuznetsov V.V., Makhova N.N., Vilkov L.V.
Journal of Physical Chemistry A, 2008
33.
Equilibrium molecular structure and spectra of 6-methyl-1,5-diazabicyclo[3.1.0]hexane: Joint analysis of gas phase electron diffraction, quantum chemistry, and spectroscopic data
Khaikin L.S., Ageev G.G., Rykov A.N., Grikina O.E., Shishkov I.F., Kochikov I.V., Kuznetsov V.V., Makhova N.N., Bukalov S.S., Leites L.A.
Physical Chemistry Chemical Physics, 2020
36.
Stereoselectivity in the Addition of 1,3-Dipolarophiles to 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes
Molchanov A.P., Sipkin D.I., Koptelov Y.B., Kopf J., Kostikov R.R.
Russian Journal of Organic Chemistry, 2003
37.
Marochkin I.I., Sharanov P.Y., Kuznetsov V.V., Shishkov I.F., Novakovskaya Y.V.
Mendeleev Communications, 2024
38.
6,6′-bis(1,5-diazabicyclo[3.1.0]hexane)
Kuznetsov V.V., Makhova N.N., Dekaprilevich M.O.
Russian Chemical Bulletin, 1999
39.
Electron diffraction study of the molecular structure for 6,6′-bis(1,5-diazabicyclo[3.1.0]hexane)
Atavin E.G., Golubinskii A.V., Popik M.V., Kuznetsov V.V., Makhova N.N., Vilkov L.V.
Journal of Structural Chemistry, 2003
41.
Equilibrium Molecular Structure of 3,3,6-trimethyl-1,5-diazabicyclo[3.1.0]hexane: the joint analysis of the gas-phase electron diffraction data and quantum chemical simulations
Ageev G.G., Rykov A.N., Grikina O.E., Shishkov I.F., Kochikov I.V., Kuznetsov V.V., Makhova N.N., Bukalov S.S.
Structural Chemistry, 2021
42.
The β-δ-Phase Transition and Thermal Expansion of Octahydro-1,3,5,7-Tetranitro-1,3,5,7-Tetrazocine
Xue C., Sun J., Kang B., Liu Y., Liu X., Song G., Xue Q.
Propellants, Explosives, Pyrotechnics, 2010
43.
Comparison of CBS-QB3, CBS-APNO, and G3 Predictions of Gas Phase Deprotonation Data
Pokon E.K., Liptak M.D., Feldgus S., Shields G.C.
Journal of Physical Chemistry A, 2001