Unraveling the sequence of electron flow along the cyclocondensation reaction between ciprofloxacin and thiosemicarbazide through the bonding evolution theory

Mbah, Maraf Bake; Adjieufack, Abel Idrice; Nguimkeu, Charnel Nguemo; Malloum, Alhadji; Zintchem, Auguste Abouem A; Bebga, Gouet; Ndassa, Ibrahim Mbouombouo

doi:10.1016/j.jmgm.2022.108141

Cited by 4 publications

(1 citation statement)

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“…To perform these analyses quantitatively, Krokidis and Silvi proposed the joint use of ELF topology [11] and Thom's catastrophe theory (CT) [14] within the Bonding Evolution Theory, BET [15,16] as a new tool for studying the electronic changes occurring along a given chemical rearrangement. BET has been used as an appropriate quantum tool to gain a deep insight into the molecular mechanisms on a wide range of chemical reactions including denitrogenations, decompositions, formation of anionic complexes, cycloadditions [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32] and even radical reactions [33].…”

Section: Introductionmentioning

confidence: 99%

Deciphering the Molecular Mechanism of Intramolecular Reactions from the Perspective of Bonding Evolution Theory

et al. 2022

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The molecular mechanisms of three intramolecular rearrangements (I, the rearrangement of allyloxycycloheptatriene to yield tricyclic ketones; II, the cycloaddition of a nitrone-alkene to render two tricyclic isoxazolidines; and III, the decomposition of N-carbamoyl-L-proline in tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione plus water, or tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole-1,3-dione plus ammonia) have been studied by means of the bonding evolution theory (BET). The thermal rearrangement I is composed by a sigmatropic rearrangement coupled to an intramolecular Diels–Alder reaction. The sigmatropic reaction comprises four steps: (1) rupture of an O-C single chemical bond, (2) transformation of a C-O single to double bond, (3) creation of pseudo-radical centers on carbon atoms coupled with a double C-C bond evolving to single and the other C-C double bond migration, and (4) formation of the new C-C single bond. For the Diels–Alder reaction, the process can be described as an initial formation of up to four monosynaptic V(C) basins in two successive steps, coupled with the loss of the double bond character of the three initial double bonds, followed by the consecutive formation of two new C-C bonds, with the new double C-C bond formation sensed in between the formation of the first and the second C-C bonds. For reaction II, the bond forming process is described by the depopulation of N-C and C-C double bonds with the creation of a V(N) and two V(C) monosynaptic basins, followed by an O-C and C-C bond-forming processes via the creation of V(O,C) and V(C,C) disynaptic basins. Finally, for the thermal decomposition III, the reaction mechanism for the water elimination takes place in four events which can be summarized as follows: (1) the depopulation of V(N) with the formation of C-N, (2) the rupture of the C-O bond with transfer of its population to V(O), (3) the restoration of an N nitrogen lone pair via H-N bond cleavage, and (4) the formation of O-H illustrating the water molecule release. For the case of deamination, the events (1) and (2) correspond to the breaking and forming process of H-O and H-N bonds, respectively, while last events deal with the C-O bond formation and the elimination of the NH3 molecule.

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Section: Introductionmentioning

confidence: 99%

Deciphering the Molecular Mechanism of Intramolecular Reactions from the Perspective of Bonding Evolution Theory

et al. 2022

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Decoding the reaction mechanism of the cyclocondensation of ethyl acetate2‐oxo‐2‐(4‐oxo‐4H‐pyrido [1.2‐a] pyrimidin‐3‐yl) polyazaheterocycle and ethylenediamine using bond evolution theory

et al. 2022

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We investigated the flow of electron density along the cyclocondensation reaction between ethyl acetate 2-oxo-2-(4-oxo-4H-pyrido[1.2-a]pyrimidin-3-yl) polyazaheterocycle (1) and ethylenediamine (2) at the ωB97XD/6-311++G(d,p) computational method within of bond evolution theory (BET). The exploration of potential energy surface shows that this reaction has three channels (1-3) with the formation of product 3 via channel-2 (the most favorable one) as the main product and this is in good agreement with experimental observations. The BET analysis allows identifying unambiguously the main chemical events happening along channel-2. The mechanism along first step (TS2-a) is described by a series of four structural stability domains (SSDs), while five SSDs for the last two steps (TS2-b and TS2-c). The first and third steps can be summarized as follows, the formation of N1-C6 bond (SSD-II), then, the restoration of the nitrogen N1 lone pair (SSD-III), and finally, the formation of the last O1-H1 bond (SSD-IV). For the second step, the formation of hydroxide ion is noted, as a result of the disappearance of V(C6,O7) basin and the transformation of C6-N1 single bond into double one

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Adsorption of Ciprofloxacin on Graphene Oxide-Based Adsorbents: Synthesis, Characterization and DFT Calculations

Sanchez,

Spaolonzi,

Cesconeto

et al. 2024

Water Air Soil Pollut

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Unraveling the sequence of electron flow along the cyclocondensation reaction between ciprofloxacin and thiosemicarbazide through the bonding evolution theory

Cited by 4 publications

References 57 publications

Deciphering the Molecular Mechanism of Intramolecular Reactions from the Perspective of Bonding Evolution Theory

Deciphering the Molecular Mechanism of Intramolecular Reactions from the Perspective of Bonding Evolution Theory

Decoding the reaction mechanism of the cyclocondensation of ethyl acetate2‐oxo‐2‐(4‐oxo‐4H‐pyrido [1.2‐a] pyrimidin‐3‐yl) polyazaheterocycle and ethylenediamine using bond evolution theory

Adsorption of Ciprofloxacin on Graphene Oxide-Based Adsorbents: Synthesis, Characterization and DFT Calculations

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