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The Chemistry of Nitrocompounds

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 April 2022) | Viewed by 28489

Special Issue Editor

Dean of Chemistry and Pharmacy Faculty, North Caucasus Federal University, Stavropol, Russia
Interests: directed synthesis; atomic accuracy; molecular complexity; structural diversity; fluorine; heterocyclic system; catalysis; biactivity; nitrocompounds
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

We cordially invite you to contribute original research papers or reviews to this Special Issue of Molecules, the topic of which is purposely defined rather broadly as the chemistry of nitrocompounds. Historically, the latter have proven to be very versatile synthetic organic chemistry intermediates, both as a means of constructing C-C or C-heteroatom bonds and as a convenient starting point for converting into many other classes of organic substances.

Nowadays, the ever-increasing use of chemicals bearing nitro groups as perspective materials, pharmaceuticals, agrochemicals etc. and/or their precursors encourage research in diverse areas to seek for new synthetic methodologies or insights on how the rich chemistry of nitro compounds could be utilized regarding the above-mentioned practical aspects.

Therefore, we see the main aim of the Special issue in sharing among the fellow scientists these kinds of findings and results. The papers you submit may cover basically any aspects of nitro group chemistry under a vaguely defined condition that presents interesting findings in the fine organic synthesis point of view. We particularly welcome studies on the application of nitro compounds in preparation of biologically active and natural carbo – and heterocyclic molecules.

Dr. Alexander V. Aksenov
Guest Editor

Manuscript Submission Information

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • new organic synthetic methods
  • nitro group transformations
  • synthesis of heterocycles
  • multicomponent reactions
  • new reagents
  • natural products
  • synthetic/atom efficiency

Published Papers (14 papers)

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Research

13 pages, 10018 KiB  
Article
Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group
by Valentine G. Nenajdenko, Namiq G. Shikhaliyev, Abel M. Maharramov, Gulnar T. Atakishiyeva, Aytan A. Niyazova, Naila A. Mammadova, Alexander S. Novikov, Ivan V. Buslov, Victor N. Khrustalev and Alexander G. Tskhovrebov
Molecules 2022, 27(16), 5110; https://doi.org/10.3390/molecules27165110 - 11 Aug 2022
Cited by 7 | Viewed by 1182
Abstract
Nitro functionalized dibromodiazadiene dyes were prepared and fully characterized including X-ray single crystal analysis. Electron deficient dibromodiazadienes were found to be able to act as donors of halogen bonding (XB), while the nitro group acted as an acceptor of the XB. Depending on [...] Read more.
Nitro functionalized dibromodiazadiene dyes were prepared and fully characterized including X-ray single crystal analysis. Electron deficient dibromodiazadienes were found to be able to act as donors of halogen bonding (XB), while the nitro group acted as an acceptor of the XB. Depending on the substituents, the Br···O XB competed with other weak interactions, and for some of the dyes, they even outcompeted the XB involving the nitro group. However, the nitro functionalized dibromoalkenes 6a and 10a, which had only the nitro moiety as the most plausible acceptor of the XB, reliably formed 1D chains via Br⋯O XB. Experimental work was supported by the DFT calculations and topological analysis of the electron density distribution within the framework of Bader’s theory (QTAIM method). Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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11 pages, 4153 KiB  
Article
Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene
by Kento Iwai, Khimiya Wada and Nagatoshi Nishiwaki
Molecules 2022, 27(15), 4804; https://doi.org/10.3390/molecules27154804 - 27 Jul 2022
Cited by 2 | Viewed by 1365
Abstract
Nitrostyrene derivatives are widely used in organic syntheses as a substrate for Michael addition, photoisomerization and cycloaddition. In contrast, ortho-hydroxy derivatives exhibit unusual behaviors in these reactions. Conjugate addition proceeded upon treatment of the ortho-hydroxy-β-nitrostyrene with an amine; however, subsequent C–C [...] Read more.
Nitrostyrene derivatives are widely used in organic syntheses as a substrate for Michael addition, photoisomerization and cycloaddition. In contrast, ortho-hydroxy derivatives exhibit unusual behaviors in these reactions. Conjugate addition proceeded upon treatment of the ortho-hydroxy-β-nitrostyrene with an amine; however, subsequent C–C bond cleavage readily occurred to afford the corresponding imine. Moreover, conversion of the trans-isomer to a cis-isomer did not occur efficiently, even when UV light was irradiated. We studied these unusual behaviors of β-nitrostyrene, focusing on the role of the ortho-hydroxy group. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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17 pages, 3371 KiB  
Article
N-Arylation of Protected and Unprotected 5-Bromo-2-aminobenzimidazole as Organic Material: Non-Linear Optical (NLO) Properties and Structural Feature Determination through Computational Approach
by Mubeen Mumtaz, Nasir Rasool, Gulraiz Ahmad, Naveen Kosar and Umer Rashid
Molecules 2021, 26(22), 6920; https://doi.org/10.3390/molecules26226920 - 17 Nov 2021
Cited by 8 | Viewed by 1880
Abstract
The interest in the NLO response of organic compounds is growing rapidly, due to the ease of synthesis, availability, and low loss. Here, in this study, Cu(II)-catalyzed selective N-arylation of 2-aminobenzimidazoles derivatives were achieved in the presence of different bases Et3N/TMEDA, [...] Read more.
The interest in the NLO response of organic compounds is growing rapidly, due to the ease of synthesis, availability, and low loss. Here, in this study, Cu(II)-catalyzed selective N-arylation of 2-aminobenzimidazoles derivatives were achieved in the presence of different bases Et3N/TMEDA, solvents DCM/MeOH/H2O, and various aryl boronic acids under open atmospheric conditions. Two different copper-catalyzed pathways were selected for N-arylation in the presence of active nucleophilic sites, providing a unique tool for the preparation of NLO materials, C-NH (aryl) derivatives of 2-aminobenzimidazoles with protection and without protection of NH2 group. In addition to NMR analysis, all synthesized derivatives (1a1f and 2a2f) of 5-bromo-2-aminobenzimidazole (1) were computed for their non-linear optical (NLO) properties and reactivity descriptor parameters. Frontier molecular orbital (FMO) analysis was performed to get information about the electronic properties and reactivity of synthesized compounds. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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11 pages, 13557 KiB  
Article
Charge Transfer Complexes of 1,3,6-Trinitro-9,10-phenanthrenequinone with Polycyclic Aromatic Compounds
by Roman Linko, Michael Ryabov, Pavel Strashnov, Pavel Dorovatovskii, Victor Khrustalev and Victor Davydov
Molecules 2021, 26(21), 6391; https://doi.org/10.3390/molecules26216391 - 22 Oct 2021
Cited by 4 | Viewed by 1392
Abstract
Understanding the interactions of organic donor and acceptor molecules in binary associates is crucial for design and control of their functions. Herein, we carried out a theoretical study on the properties of charge transfer complexes of 1,3,6-trinitro-9,10-phenanthrenequinone (PQ) with 23 aromatic π-electron donors. [...] Read more.
Understanding the interactions of organic donor and acceptor molecules in binary associates is crucial for design and control of their functions. Herein, we carried out a theoretical study on the properties of charge transfer complexes of 1,3,6-trinitro-9,10-phenanthrenequinone (PQ) with 23 aromatic π-electron donors. Density functional theory (DFT) was employed to obtain geometries, frontier orbital energy levels and amounts of charge transfer in the ground and first excited states. For the most effective donors, namely, dibenzotetrathiafulvalene, pentacene, tetrathiafulvalene, 5,10-dimethylphenazine, and tetramethyl-p-phenylenediamine, the amount of charge transfer in the ground state was shown to be 0.134−0.240 e. Further, a novel charge transfer complex of PQ with anthracene was isolated in crystalline form and its molecular and crystal structure elucidated by single-crystal synchrotron X-ray diffraction. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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16 pages, 3481 KiB  
Article
Direct Conversion of 3-(2-Nitroethyl)-1H-Indoles into 2-(1H-Indol-2-yl)Acetonitriles
by Alexander V. Aksenov, Nicolai A. Aksenov, Elena V. Aleksandrova, Dmitrii A. Aksenov, Igor Yu. Grishin, Elena A. Sorokina, Allison Wenger and Michael Rubin
Molecules 2021, 26(20), 6132; https://doi.org/10.3390/molecules26206132 - 11 Oct 2021
Cited by 4 | Viewed by 2227
Abstract
The recently discovered [4+1]-spirocyclization of nitroalkenes to indoles provided a convenient new approach to 2-(1H-indol-2-yl)acetonitriles. However, this reaction was complicated by the formation of inert 3-(2-nitroethyl)-1H-indole byproducts. Herein, we offer a workaround this problem that allows for effective transformation [...] Read more.
The recently discovered [4+1]-spirocyclization of nitroalkenes to indoles provided a convenient new approach to 2-(1H-indol-2-yl)acetonitriles. However, this reaction was complicated by the formation of inert 3-(2-nitroethyl)-1H-indole byproducts. Herein, we offer a workaround this problem that allows for effective transformation of the unwanted byproducts into acetonitrile target molecules. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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14 pages, 2553 KiB  
Article
Electrophilically Activated Nitroalkanes in Double Annulation of [1,2,4]Triazolo[4,3-a]quinolines and 1,3,4-Oxadiazole Rings
by Alexander V. Aksenov, Nikita K. Kirilov, Nicolai A. Aksenov, Dmitrii A. Aksenov, Elena A. Sorokina, Carolyn Lower and Michael Rubin
Molecules 2021, 26(18), 5692; https://doi.org/10.3390/molecules26185692 - 20 Sep 2021
Cited by 4 | Viewed by 2510
Abstract
Nitroalkanes activated with polyphosphoric acid could serve as efficient electrophiles in reactions with amines and hydrazines, enabling various cascade transformations toward heterocyclic systems. This strategy was developed for an innovative synthetic protocol employing simultaneous or sequential annulation of two different heterocyclic cores, affording [...] Read more.
Nitroalkanes activated with polyphosphoric acid could serve as efficient electrophiles in reactions with amines and hydrazines, enabling various cascade transformations toward heterocyclic systems. This strategy was developed for an innovative synthetic protocol employing simultaneous or sequential annulation of two different heterocyclic cores, affording [1,2,4]triazolo[4,3-a]quinolines with 1,3,4-oxadiazole substituents. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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10 pages, 3903 KiB  
Article
Nitropyridines as 2π-Partners in 1,3-Dipolar Cycloadditions with N-Methyl Azomethine Ylide: An Easy Access to Condensed Pyrrolines
by Maxim A. Bastrakov, Alexey K. Fedorenko, Alexey M. Starosotnikov and Alexander Kh. Shakhnes
Molecules 2021, 26(18), 5547; https://doi.org/10.3390/molecules26185547 - 13 Sep 2021
Cited by 2 | Viewed by 1532
Abstract
1,3-Dipolar cycloaddition reactions of 2-substituted 5-R-3-nitropyridines and isomeric 3-R-5-nitropyridines with N-methyl azomethine ylide were studied. The effect of the substituent at positions 2 and 5 of the pyridine ring on the possibility of the [3+2]-cycloaddition process was revealed. A [...] Read more.
1,3-Dipolar cycloaddition reactions of 2-substituted 5-R-3-nitropyridines and isomeric 3-R-5-nitropyridines with N-methyl azomethine ylide were studied. The effect of the substituent at positions 2 and 5 of the pyridine ring on the possibility of the [3+2]-cycloaddition process was revealed. A number of new derivatives of pyrroline and pyrrolidine condensed with a pyridine ring were synthesized. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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17 pages, 2936 KiB  
Article
Redox Conversions of 5-Methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4triazolo[1,5-a]pyrimidinide L-Arginine Monohydrate as a Promising Antiviral Drug
by Alexandra Ivoilova, Ludmila V. Mikhalchenko, Anton Tsmokalyuk, Marina Leonova, Andrey Lalov, Polina Mozharovskaia, Alisa N. Kozitsina, Alla V. Ivanova and Vladimir L. Rusinov
Molecules 2021, 26(16), 5087; https://doi.org/10.3390/molecules26165087 - 22 Aug 2021
Cited by 6 | Viewed by 1919
Abstract
This article presents the results of a study of electrochemical transformations in aqueous and aprotic media of 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidinide l-arginine monohydrate (1a, Triazid) obtained by electrochemical methods and ESR spectroscopy. The effect of pH on the current and the reduction potential of [...] Read more.
This article presents the results of a study of electrochemical transformations in aqueous and aprotic media of 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidinide l-arginine monohydrate (1a, Triazid) obtained by electrochemical methods and ESR spectroscopy. The effect of pH on the current and the reduction potential of 1a in an aqueous Britton–Robinson buffer solution was studied. It was found that 1a is irreversibly reduced in aqueous acidic media on a glassy carbon electrode in one stage with the participation of six electrons and the formation of 5-methyl-6-amino-7-oxo-1,2,4-triazolo[1,5-a]pyrimidin. The electroreduction of 1a in DMF on a background of tetrabutylammonium salts proceeds in two stages, controlled by the kinetics of second-order reactions. In the first stage, the reduction of 1a is accompanied by protonation by the initial compound of the basic intermediate products formed in the electrode reaction (self-protonation mechanism). The second quasi-reversible stage of the electroreduction 1a corresponds to the formation of a dianion radical upon the reduction of the heterocyclic anion 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidin, which is formed upon the potentials of the first peak. The ESR spectrum of the radical dianion was recorded upon electroreduction of Triazid in the presence of Bu4NOH. The effect of the formation of ion pairs on the reversibility of the second peak of the 1a transformation is shown. A change in the rate and regioselectivity of the protonation of the dianion radical in the presence of Na+ and Li+ ions is assumed. The results of studying the electroreduction of 1a by ESR spectroscopy with a TEMPO trap make it possible to assume the simultaneous formation of both a nitroxyl radical and a radical with the spin density localized on the nitrogen at the 4 position of the six-membered ring. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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15 pages, 1511 KiB  
Article
An Efficient Synthesis of 2-CF3-3-Benzylindoles
by Vasiliy M. Muzalevskiy, Zoia A. Sizova and Valentine G. Nenajdenko
Molecules 2021, 26(16), 5084; https://doi.org/10.3390/molecules26165084 - 22 Aug 2021
Cited by 2 | Viewed by 2157
Abstract
The reaction of α-CF3-β-(2-nitroaryl) enamines with benzaldehydes afforded effectively α,β-diaryl-CF3-enones having nitro group. Subsequent reduction of nitro group by NH4HCO2-Pd/C system initiated intramolecular cyclization to give 2-CF3-3-benzylindoles. Target products can be prepared in [...] Read more.
The reaction of α-CF3-β-(2-nitroaryl) enamines with benzaldehydes afforded effectively α,β-diaryl-CF3-enones having nitro group. Subsequent reduction of nitro group by NH4HCO2-Pd/C system initiated intramolecular cyclization to give 2-CF3-3-benzylindoles. Target products can be prepared in up to quantitative yields. Broad synthetic scope of the reaction was shown. Probable mechanism of indole formation is proposed. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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19 pages, 4702 KiB  
Article
Oxidative Aromatization of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines: Synthetic Possibilities and Limitations, Mechanism of Destruction, and the Theoretical and Experimental Substantiation
by Daniil N. Lyapustin, Evgeny N. Ulomsky, Ilya A. Balyakin, Alexander V. Shchepochkin, Vladimir L. Rusinov and Oleg N. Chupakhin
Molecules 2021, 26(16), 4719; https://doi.org/10.3390/molecules26164719 - 04 Aug 2021
Cited by 5 | Viewed by 1893
Abstract
The reaction tolerance of the multicomponent process between 3-aminoazoles, 1-morpholino-2-nitroalkenes, and aldehydes was studied. The main patterns of this reaction have been established. Conditions for the oxidation of 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines were selected. Previous claims that the 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines could not be aromatised have now been [...] Read more.
The reaction tolerance of the multicomponent process between 3-aminoazoles, 1-morpholino-2-nitroalkenes, and aldehydes was studied. The main patterns of this reaction have been established. Conditions for the oxidation of 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines were selected. Previous claims that the 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines could not be aromatised have now been refuted. Compounds with an electron-donor substituent at position seven undergo decomposition during oxidation. The phenomenon was explained based on experimental data, electro-chemical experiment, and quantum-chemical calculation. The mechanism of oxidative degradation has been proposed. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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15 pages, 1587 KiB  
Article
Electrophilically Activated Nitroalkanes in Synthesis of 3,4-Dihydroquinozalines
by Alexander V. Aksenov, Igor Yu. Grishin, Nicolai A. Aksenov, Vladimir V. Malyuga, Dmitrii A. Aksenov, Mezvah A. Nobi and Michael Rubin
Molecules 2021, 26(14), 4274; https://doi.org/10.3390/molecules26144274 - 14 Jul 2021
Cited by 3 | Viewed by 2576
Abstract
Nitroalkanes activated with polyphosphoric acid serve as efficient electrophiles in reactions with various nucleophilic amines. Strategically placed second functionality allows for the design of annulation reactions enabling preparation of various heterocycles. This strategy was employed to develop an innovative synthetic approach towards 3,4-dihydroquinazolines [...] Read more.
Nitroalkanes activated with polyphosphoric acid serve as efficient electrophiles in reactions with various nucleophilic amines. Strategically placed second functionality allows for the design of annulation reactions enabling preparation of various heterocycles. This strategy was employed to develop an innovative synthetic approach towards 3,4-dihydroquinazolines from readily available 2-(aminomethyl)anilines. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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9 pages, 3306 KiB  
Communication
Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization
by Mao-Xi Zhang, Nathaniel B. Zuckerman, Philip F. Pagoria, Bradley A. Steele, I-Feng Kuo, Gregory H. Imler and Damon Parrish
Molecules 2021, 26(14), 4209; https://doi.org/10.3390/molecules26144209 - 11 Jul 2021
Cited by 6 | Viewed by 2434
Abstract
Mono- and dinitro-BN-naphthalenes, i.e., 1-nitro-, 3-nitro-, 1,6-dinitro-, 3,6-dinitro-, and 1,8-dinitro-BNN, were generated in the nitration of 9,10-BN-naphthalene (BNN), a boron–nitrogen (BN) bond-embedded naphthalene, with AcONO2 and NO2BF4 in acetonitrile. The nitrated products were isolated and characterized by NMR, GC-MS, [...] Read more.
Mono- and dinitro-BN-naphthalenes, i.e., 1-nitro-, 3-nitro-, 1,6-dinitro-, 3,6-dinitro-, and 1,8-dinitro-BNN, were generated in the nitration of 9,10-BN-naphthalene (BNN), a boron–nitrogen (BN) bond-embedded naphthalene, with AcONO2 and NO2BF4 in acetonitrile. The nitrated products were isolated and characterized by NMR, GC-MS, IR, and X-ray single crystallography. The effects of the nitration on the electron density and aromaticity of BNN were evaluated by B-11 NMR analysis and HOMA calculations. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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16 pages, 460 KiB  
Article
Computational Study of the Electron Spectra of Vapor-Phase Indole and Four Azaindoles
by Delano P. Chong
Molecules 2021, 26(7), 1947; https://doi.org/10.3390/molecules26071947 - 30 Mar 2021
Cited by 3 | Viewed by 1791
Abstract
After geometry optimization, the electron spectra of indole and four azaindoles are calculated by density functional theory. Available experimental photoemission and excitation data for indole and 7-azaindole are used to compare with the theoretical values. The results for the other azaindoles are presented [...] Read more.
After geometry optimization, the electron spectra of indole and four azaindoles are calculated by density functional theory. Available experimental photoemission and excitation data for indole and 7-azaindole are used to compare with the theoretical values. The results for the other azaindoles are presented as predictions to help the interpretation of experimental spectra when they become available. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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12 pages, 2603 KiB  
Article
New Nitro-Laterally Substituted Azomethine Derivatives; Synthesis, Mesomorphic and Computational Characterizations
by Mohamed A. El-atawy, Magdi M. Naoum, Salma A. Al-Zahrani and Hoda A. Ahmed
Molecules 2021, 26(7), 1927; https://doi.org/10.3390/molecules26071927 - 30 Mar 2021
Cited by 28 | Viewed by 1668
Abstract
Two new homologues series, based on two rings of the azomethine central group bearing the terminal alkoxy group of various chain lengths, were prepared. The alkoxy chain length varied between 6 and 16 carbons. The other terminal wing in the first series was [...] Read more.
Two new homologues series, based on two rings of the azomethine central group bearing the terminal alkoxy group of various chain lengths, were prepared. The alkoxy chain length varied between 6 and 16 carbons. The other terminal wing in the first series was the F atom, and the compound is named N-4-florobenzylidene-4-(alkoxy)benzenamine (In). The second group of compounds included a lateral NO2 substituent in addition to the terminal F atom, named N-(4-fluoro-3-nitrobenzylidene)-4-(alkyloxy)aniline (IIn). Mesomorphic and optical properties were carried out via differential scanning calorimetry (DSC) and polarized optical microscopy (POM). Elemental analyses, FT-IR, and NMR spectroscopy were carried out to elucidate the molecular structures of the synthesized groups. Mesomorphic investigations indicated that all the synthesized homologues (In) were monomorphic, possessing the smectic A (SmA) phase monotropically, while the second group (IIn) members were non-mesomorphic. The experimental data indicated that the formation of the mesophase is affected by the protrusion of the lateral nitro group. The disruption of the mesophase in the second group was attributed to the increase of its molecular width, which affects its lateral intermolecular interactions. The computational simulations were in agreement with the experimental data. On the other hand, the location of NO2 group within the molecular geometry increased the melting temperature of the molecule, and thus, affected their thermal and physical properties. By discussing the estimated parameters, it was found that the molecular architecture, the dipole moment, and the polarizability of the investigated compounds are highly affected by the electronic nature and position of the terminal and lateral substituents as well as their volumes. Full article
(This article belongs to the Special Issue The Chemistry of Nitrocompounds)
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