☆ 4.1 Article

A tetrazol-5-yl analogue of glycine, 5-ammoniomethyl-1H-tetrazolide, and its copper(II) complex

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY (2010)

Journal

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY

Volume 66, Issue -, Pages M22-M25

Publisher

INT UNION CRYSTALLOGRAPHY

DOI: 10.1107/S0108270109055164

Keywords

-

Categories

Chemistry, Multidisciplinary Crystallography

Ask authors/readers for more resources

Protocol

Community support

Reagent

Community support

Abstract

A nonclassical tetrazole isostere of glycine, viz. zwitterionic 5-ammoniomethyl-1H-tetrazolide, C2H5N5, (I), crystallizes in the chiral P3(1) space group, similar to gamma-glycine. The crystal packing of (I) is determined by a set of classical hydrogen bonds, forming a three-dimensional network that is practically the same as that in gamma-glycine. The Cu-II complex of (I), poly-[[ bis(mu(2)-5-aminomethyl-1H-tetrazolido-kappa N-3(1),N-5:N-4) copper(II)] dihydrate], {[Cu(C2H4N5)(2)]center dot 2H(2)O}(n), (II), is a layered coordination polymer formed as a result of tetrazole ring bridges. The Cu-II cations lie on inversion centres, are surrounded by four anions and adopt elongated octahedral coordination. Water molecules are located in the interlayer space and connect the layers into a three-dimensional network via a system of hydrogen bonds.

Authors

I am an author on this paper

Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.1

Not enough ratings

Secondary Ratings

Novelty

-

Significance

-

Scientific rigor

-

Rate this paper

Recommended

Article Engineering, Environmental

One-step synthesis to an insensitive explosive: N,N'-bis((1H-tetrazol-5-yl) methyl)nitramide (BTMNA)

Gang Zhao, Ping Yin, Richard Staples, Jeanne M. Shreeve

Summary: In this study, an insensitive and high performing explosive BTMNA was synthesized as a practical replacement for RDX. BTMNA exhibits remarkable performance with high detonation velocity and pressure, making it a promising alternative to RDX.

CHEMICAL ENGINEERING JOURNAL (2021)

Add to Collection

Article Chemistry, Medicinal

ω-(5-Phenyl-2H-tetrazol-2-yl)alkyl-substituted hydrazides and related compounds as inhibitors of amine oxidase copper containing 3 (AOC3)

Florian Galster, Timo Poestges, Walburga Hanekamp, Matthias Lehr

Summary: Amine oxidase copper containing 3 (AOC3) is an important enzyme that plays a potential role in the treatment of inflammation-related diseases by facilitating the transmigration of inflammatory cells from blood vessels to tissues. By modifying the functional groups of known AOC3 inhibitors, novel inhibitors can be obtained and further optimized through structural modifications.

ARCHIV DER PHARMAZIE (2022)

Add to Collection

Article Chemistry, Organic

1,3,5-Tris[(2H-tetrazol-5-yl)methyl]isocyanurate and Its Tricationic Salts as Thermostable and Insensitive Energetic Materials

Parasar Kumar, Vikas D. Ghule, Srinivas Dharavath

Summary: Various energetic salts were obtained from inexpensive starting materials via a simple and efficient synthetic route. These compounds showed excellent detonation properties, high nitrogen content, high positive heats of formation, good thermostability, and remarkable insensitivity.

ORGANIC LETTERS (2022)

Add to Collection

Article Chemistry, Medicinal

3-(1,2,3-Triazol-4-yl)-β-Carbolines and 3-(1H-Tetrazol-5-yl)-β-Carbolines: Synthesis and Evaluation as Anticancer Agents

Joao L. P. Ribeiro, Joana B. Loureiro, Susana M. M. Lopes, Lucilia Saraiva, Teresa M. V. D. Pinho e Melo

Summary: This study focuses on the synthesis and evaluation of novel beta-carbolines as potential anticancer agents. The researchers successfully synthesized tryptophan analogs by reacting nitrosoalkenes with indole, and subsequently obtained 3-(1,2,3-triazol-4-yl)-beta-carbolines through condensation and oxidation reactions. The synthesized compounds were then tested for their antiproliferative activity against colorectal cancer cell lines, with the 3-(1H-tetrazol-5-yl)-beta-carbolines showing the highest potency. Further studies demonstrated that a tetrazolyl-beta-carboline derivative exhibited high selectivity and potent activity against various cancer cell lines. This work highlights the potential of 3-tetrazolyl-beta-carboline as a promising anticancer agent for future investigation.

PHARMACEUTICALS (2022)

Add to Collection

Article Chemistry, Organic

Nucleophile-Induced Rearrangement of 2H-Azirine-2-carbonyl Azides to 2-(1H-Tetrazol-1-yl)acetic Acid Derivatives

Nikita I. Efimenko, Olesya A. Tomashenko, Dar'ya V. Spiridonova, Mikhail S. Novikov, Alexander F. Khlebnikov

Summary: 2H-azirine-2-carbonyl azides undergo rearrangement into derivatives of 2-(1H-tetrazol-1-yl)acetic acid when interacting with O- and S-nucleophiles at room temperature. The reaction is catalyzed by tertiary amines or hydrazoic acid. Different reactions occur when interacting with primary alcohols and phenols, leading to the formation of alkyl/aryl 2-(1H-tetrazol-1-yl)acetates. Additionally, thiophenols react with 2H-azirine-2-carbonyl azides to produce S-aryl 2-(1H-tetrazol-1yl)ethanethioates. The mechanism of these nucleophile-induced rearrangements is discussed based on DFT calculations, kinetic experiments, and N-15 labeling experiments.

ORGANIC LETTERS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Metal-free regioselective construction of 2-aryl-2H-tetrazol-5-yl difluoromethylene phosphonates

Shi-Jing Zhai, Dominique Cahard, Fa-Guang Zhang, Jun-An Ma

Summary: Three bench-stable difluoromethylene phosphonate hydrazones were synthesized in good yields from simple diethyl(difluoromethyl)phosphonate within two steps. The [3 + 2] cycloaddition reaction with aryl diazonium salts under metal-free conditions exhibited exclusive regioselectivity. This method provides practical access to a wide range of 2-aryl-2H-tetrazol-5-yl difluoromethylene phosphonates, including derivatives of amino acids and drug cores.

CHINESE CHEMICAL LETTERS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Alkaline metal and alkaline earth metal salts of di(1H-tetrazol-5-yl)methanone (DTO): energetic catalysts for ammonium perchlorate decomposition

Haibo Li, Yanna Wang, Zhenghe Wei, Lianghong Xia, Zhimin Li, Tonglai Zhang

Summary: Novel coordination complexes for promising energetic materials were synthesized and characterized. These compounds exhibited good thermal properties and catalytic performances, making them potential combustion catalysts for composite propellants.

NEW JOURNAL OF CHEMISTRY (2022)

Add to Collection

Article Biochemistry & Molecular Biology

N-(3-cyano-1H-indol-5-yl)isonicotinamide and N-(3-cyano-1H-indol-5-yl)-1H-benzo[d]imidazole-5-carboxamide derivatives: Novel amide-based xanthine oxidase inhibitors

Shun Tu, Ting-Jian Zhang, Yi Zhang, Xu Zhang, Zhen-Hao Zhang, Fan-Hao Meng

Summary: This study synthesized two series of amide-based XO inhibitors, with compound 3i showing the most promising in vitro inhibitory potency and hypouricemic effect. Molecular simulations provided insights into the interaction modes of representative compounds, supporting compound 3i as a lead for further exploration of amide-based XO inhibitors.

BIOORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Crystal structures and properties of high-nitrogen energetic salts based on (Z)-1,1-diamino-2-nitro-2-(1H-tetrazol-5-yl)ethene

Zhaoyang Yin, Yaqun Dong, Zhiwei Zeng, Wei Huang, Yongxing Tang

Summary: Three energetic salts based on (Z)-1,1-diamino-2-nitro-2-(1H-tetrazol-5-yl)ethene were designed and prepared, fully characterized, and their detonation performances were calculated. These salts showed good thermal stabilities and relatively insensitive characteristics, making them promising energetic materials for future applications.

NEW JOURNAL OF CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Azirine-triazole hybrids: selective synthesis of 5-(2H-azirin-2-yl)-, 5-(1H-pyrrol-2-yl)-1H-1,2,3-triazoles and 2-(5-(2H-azirin-2-yl)-1H-1,2,3-triazol-1-yl)pyridines

Yulia Krivolapova, Olesya A. Tomashenko, Liya D. Funt, Dar'ya Spiridonova, Mikhail S. Novikov, Alexander F. Khlebnikov

Summary: Azirine-triazole hybrids were selectively synthesized under different reaction conditions and the reaction mechanism and selectivity were discussed based on DFT calculations.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Add to Collection

Article Biochemical Research Methods

Theoretical studies on 2,3,5,6-Tetra(1H-tetrazol-5-yl)pyrazine and 1,1-dia- mino-2,2-Dinitroethylene blending system

Jun Li, Tao Zhou, Jing Chen, Xiaojun Wang, Yueyang Wang, Wendong Liu, Xinhui Zhang, Zongchang Li, Xinan Chen, Jingwei Han, Chan Kyung Kim

Summary: The properties of the H4TTP and FOX-7 blending system were studied using molecular dynamics simulations. It was found that the HOMO of H4TTP is distributed on the pyrazine and tetrazole rings, while the HOMO of FOX-7 is mainly located on the C-C bonds. The mechanical properties and cohesive energy densities of the blending system were different from those of the monomers, which improved the sensitivity of H4TTP and the safety of explosives.

JOURNAL OF MOLECULAR GRAPHICS & MODELLING (2022)

Add to Collection

Article Biochemistry & Molecular Biology

6-(Tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as Novel Potent CK2 Inhibitors

Grigoriy V. V. Urakov, Konstantin V. V. Savateev, Svetlana K. K. Kotovskaya, Vladimir L. L. Rusinov, Alexandr A. A. Spasov, Denis A. A. Babkov, Elena V. V. Sokolova

Summary: The study focuses on the synthesis and structure-activity relationship of 6-(tetrazol-5-yl)-7-aminoazolo[1,5-a]pyrimidines as inhibitors of Casein kinase 2 (CK2); The desired compounds showed significant CK2 inhibition, with the leader compound displaying an IC50 of 45 nM.

MOLECULES (2022)

Add to Collection

Article Chemistry, Physical

A new coordination compound based on 3, 3′-bis(1H-tetrazol-5-yl)-4, 4′-azofurazan (H2BTZAF): Preparation, crystal structure, and thermal properties

Chenli Wei, Zeyu Guo, Yongjie Li, Jie Huang

Summary: A new nitrogen-rich energetic complex Cd(DMF)(2)BTZAF (1) was synthesized and characterized. The crystal structure revealed a distorted octahedral coordination of Cd2+ ion. Thermal decomposition studies showed compound 1's stability and insensitivity.

JOURNAL OF MOLECULAR STRUCTURE (2022)

Add to Collection

Article Chemistry, Medicinal

Discovery of 3-(4-(2-((1H-Indol-5-yl)amino)-5-fluoropyrimidin-4yl)-1H-pyrazol-1-yl)propanenitrile Derivatives as Selective TYK2 Inhibitors for the Treatment of Inflammatory Bowel Disease

Chufeng Zhang, Wenyan Qi, Yong Li, Minghai Tang, Tao Yang, Kongjun Liu, Yong Chen, Dexin Deng, Mingli Xiang, Lijuan Chen

Summary: The study introduces a novel TYK2 inhibitor, compound 14l, which exhibits potent inhibition and selectivity, and shows potential efficacy in the treatment of immune-mediated diseases.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Group 11 metal complexes of the dinucleating triazole appended bisphosphine 1,4-bis (5-(diisopropylphosphaneyl)-1-phenyl-1H-1,2,3-triazol-4-yl)benzene

Basvaraj S. Kote, Harish S. Kunchur, Latchupatula Radhakrishna, Madhusudan K. Pandey, Maravanji S. Balakrishna

Summary: The synthesis of a triazole appended dinucleating bisphosphine and its coinage metal complexes were described, including dimeric copper complexes, hetero-cubane silver complex, disilver complexes, dinuclear acetate bridged silver complex, and digold complex. The molecular structures of these complexes were confirmed by single crystal X-ray analysis, showing non-covalent interactions between copper and C-arene.

DALTON TRANSACTIONS (2021)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Polymeric chain complexes of copper(II) chloride with 1,5-disubstituted tetrazoles: Structure and magnetic properties

Sergei V. Voitekhovich, Yuri Grigoriev, Alexander S. Lyakhov, Ludmila S. Ivashkevich, Jennifer Klose, Berthold Kersting, Oleg A. Ivashkevich

Summary: Three new copper(II) complexes were synthesized and their structures and magnetic properties were revealed through X-ray analysis. The copper(II) ions in the complexes exhibit antiferromagnetic coupling, forming coordination polymers with specific structures.

POLYHEDRON (2021)

Add to Collection

Article Chemistry, Organic

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV-vis spectra, and DFT calculations

Vladislav A. Budevich, Sergei V. Voitekhovich, Alexander V. Zuraev, Vadim E. Matulis, Vitaly E. Matulis, Alexander S. Lyakhov, Ludmila S. Ivashkevich, Oleg A. Ivashkevich

Summary: Tetrazolium-5-aminides were prepared by tert-butylation reaction and characterized for their structural and spectral features. The substitution reactions successfully yielded tetrazolium salts or conjugate aminides.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Direct Synthesis and Characterization of Copper(II) 1-Phenyltetrazol-5-olates

Sergei V. Voitekhovich, Alexander S. Lyakhov, Ludmila S. Ivashkevich, Alexander N. Lavrov, Ludmila G. Lavrenova, Oleg A. Ivashkevich

Summary: The interaction of 1-phenyl-1,4-dihydro-5H-tetrazol-5-one (Hpto) with ethylenediamine (en) and metallic copper in ethanol in the open air yields different molecular complexes, with the tetrazol-5-one ligand exhibiting different coordination states. The binuclear complex shows paramagnetism with weak antiferromagnetic exchange interaction between copper ions.

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE (2021)

Add to Collection

Article Chemistry, Physical

Thermodynamic Properties of Some Functionally Substituted Azoles in the Condensed State

A. Blokhin, Ya N. Yurkshtovich, E. N. Stepurko, D. Shiman, A. Zuraev, S. V. Voitekhovich

Summary: The heat capacity of several compounds was measured at different temperatures using low-temperature adiabatic calorimetry. The thermodynamic parameters of phase transitions were determined for these compounds, and the standard thermodynamic functions in the crystalline and liquid states were calculated.

RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A (2022)

Add to Collection

Article Chemistry, Inorganic & Nuclear

5-Amino-2-isopropenyltetrazole and its Cupric Chloride Complex: Synthesis, Structure and Magnetism

Sergei V. Voitekhovich, Alexander S. Lyakhov, Ludmila S. Ivashkevich, Vadim E. Matulis, Yuri Grigoriev, Jennifer Klose, Berthold Kersting, Oleg A. Ivashkevich

Summary: In this study, a new tetrazole ligand, 5-amino-2-isopropenyltetrazole, was synthesized and found to form a complex with copper(II) chloride. Through experimental and analytical methods, the mechanism of action and structural characteristics of the ligand in the complex were revealed, showing weak antiferromagnetic coupling of copper(II) ions.

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE (2022)

Add to Collection

Article Chemistry, Inorganic & Nuclear

2,6-Di(1H-tetrazol-1-yl)pyridine and its cupric chloride complex

Evgeny Y. Grigoryev, Inna M. Grigorieva, Alexander S. Lyakhov, Ludmila S. Ivashkevich, Vadim E. Matulis, Ludmila G. Lavrenova, Sergei V. Voitekhovich, Yuri Grigoriev

Summary: 2,6-Di(1H-tetrazol-1-yl)pyridine (DTP) was synthesized and its structure and coordination behavior were studied. The results showed that DTP adopts the thermodynamically most stable conformation and its pyridine ring nitrogen atom does not participate in coordination or intermolecular hydrogen bonding.

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE (2023)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Dicopper(II) complexes with N3,N4-bridging 1-alkyltetrazoles: Synthesis, crystal structure, magnetic and thermodynamic properties

Sergei V. Voitekhovich, Alexander S. Lyakhov, Mikhail M. Degtyarik, Yuri Grigoriev, Dmitriy I. Shiman, Jennifer Klose, Elena N. Stepurko, Andrey Blokhin, Ludmila S. Ivashkevich, Berthold Kersting, Oleg A. Ivashkevich

Summary: 1-R-Tetrazoles (R = Et, i-Pr, t-Bu) react with copper(II) tetrafluoroborate hexahydrate and copper(II) nitrate tetrahydrate to form complexes [Cu2L8(H2O)(2)]X-4, where L = 1-R-tetrazole and X = BF4 or NO3. The complexes are dinuclear cations [Cu2L8(H2O)(2)](4+), with six tetrazole ligands coordinating in a monodentate N4 fashion and two providing N-3,N-4 bridges between the copper(II) cations; water molecules complete the coordination of metal ions. Magnetic susceptibility measurements indicate weak antiferromagnetic coupling between the copper(II) ions. The complex [Cu2L8(H2O)(2)](BF4)(4) (L = 1-isopropyltetrazole) undergoes a temperature induced reversible single-crystal to single-crystal polymorphic phase transition. The standard thermodynamic characteristics of this transition as well as the standard thermodynamic functions of the compound in the temperature range of 80-370 K were determined using adiabatic calorimetry. Additionally, a mononuclear complex [CuL6](BF4)(2) (L = 1-ethyltetrazole) was obtained and structurally characterized during the investigation.

JOURNAL OF SOLID STATE CHEMISTRY (2023)

Add to Collection

No Data Available

© Peeref 2019-2024. All rights reserved.