Skip to content
2000
  1. Home
  2. A-Z Publications
  3. Current Organic Synthesis
  4. Volume 22, Issue 3
  5. Article
Volume 22, Issue 3
  • ISSN: 1570-1794
  • E-ISSN: 1875-6271

Abstract

Introduction

The reaction between 4-hydroxy-3,5-dimethoxyenzaldehyde and 2-ni-troaniline has been discovered, and the final product has been identified such as 2-6-dimethoxy-4-((2-nitrophenylimin)methyl)phenol (C1).

Materials and Methods

X-ray diffraction examination performed on a single crystal provided conclusive evidence regarding the structure. Crystallography reveals that the two molecules A and B that were enclosed within the asymmetric unit are structurally distinct from one another. C-H·O, N-H·O, and O-H·O bonding is primarily responsible for the crystal packing stability. H-O and off-set stacking interactions also contribute to the crystal packing's overall stability.

Results

To do further research into the intermolecular interactions, the Hirshfeld surface analysis technique is utilized. It is possible to determine the partiality of the interatomic contacts to create crystal packing interactions by computing the improvement ratio for those contacts. In addition, computational research is carried out with the B3LYP/6-31G(d,p) model to determine the amount of energy that is required for molecular pairs to interact.

Conclusion

The study concluded the roles those different kinds of interaction energy play in maintaining the stability of the molecular pair.

© 2025 Bentham Science Publishers
Loading

Article metrics loading...

/content/journals/cos/10.2174/0115701794309830240529042210
2024-09-27
2025-05-12

  • From This Site

    /content/journals/cos/10.2174/0115701794309830240529042210
    dcterms_title,dcterms_subject,pub_keyword
    -contentType:Contributor -contentType:Concept -contentType:Institution
    10
    5
Loading full text...

Full text loading...

References

  1. BjørsvikH.R. MinisciF. Fine chemicals from lignosulfonates. 1. Synthesis of vanillin by oxidation of lignosulfonates.Org. Process Res. Dev.19993533034010.1021/op9900028
     [Google Scholar]
  2. GendronD. Vanillin: A promising biosourced building block for the preparation of various heterocycles.Front Chem.202210July94935510.3389/fchem.2022.94935535873060
     [Google Scholar]
  3. ChohanZ.H. MunawarA. SupuranC.T. Transition metal ion complexes of Schiff-bases. Synthesis, characterization and antibacterial properties.Met. Based Drugs20018313714310.1155/MBD.2001.13718475987
     [Google Scholar]
  4. KhanpourM. Taghvaei- GanjaliS. ZadmardR. Amino acid derivative of calix[4]arene as Schiff base for sensing of copper(II).Orient. J. Chem.201733127428110.13005/ojc/330132
     [Google Scholar]
  5. MetzlerC.M. ViswanathR. MetzlerD.E. Equilibria and absorption spectra of tryptophanase.J. Biol. Chem.1991266159374938110.1016/S0021‑9258(18)92829‑22033039
     [Google Scholar]
  6. PatelR.V. PanchalJ.G. MenonS.K. Synthesis and study of binuclear calix[4]arene Schiff base Co(II) complexes as catalyst in the presence of PhIO for the catalytic oxidation of olefin.J. Incl. Phenom. Macrocycl. Chem.2010671-2637110.1007/s10847‑009‑9669‑8
     [Google Scholar]
  7. ShijuC. ArishD. BhuvaneshN. KumaresanS. Synthesis, characterization, and biological evaluation of Schiff base-platinum(II) complexes.Spectrochim. Acta Part A Mol. Biomol. Spectrosc.201514521322210.1016/j.saa.2015.02.030
     [Google Scholar]
  8. TuckerJ.L. Green chemistry, a pharmaceutical perspective.Org. Process Res. Dev.200610231531910.1021/op050227k
     [Google Scholar]
  9. AlamM.Z. KhanS.A. A review on Rhodamine-based Schiff base derivatives: synthesis and fluorescent chemo-sensors behaviour for detection of Fe 3+ and Cu 2+ ions.J. Coord. Chem.2023763-437140210.1080/00958972.2023.2183852
     [Google Scholar]
  10. FatimaZ. BashaH.A. KhanS.A. A review: An overview on third-order nonlinear optical and optical limiting properties of Schiff bases.J. Mol. Struct.2023129213606210.1016/j.molstruc.2023.136062
     [Google Scholar]
  11. WeiD. LiN. LuG. YaoK. Synthesis, catalytic and biological activity of novel dinuclear copper complex with Schiff base.Sci. China B Chem.200649322522910.1007/s11426‑006‑0225‑8
     [Google Scholar]
  12. BelghithS. BahrouniY. Ben HamadaL. Synthesis, crystal structure and characterization of a new dihydrogenomonophosphate: (C7H9N2O)H2PO4.Open J. Inorg. Chem.201554122130
     [Google Scholar]
  13. RamalingamA. KansızS. DegeN. SambandamS. Synthesis, crystal structure, dft calculations and hirshfeld surface analysis of 3-chloro-2,6-bis(4-chlorophenyl)-3-methylpiperidin-4-one.J. Chem. Crystallogr.202151227328710.1007/s10870‑020‑00852‑3
     [Google Scholar]
  14. SheldrickG.M. SHELXT – Integrated space-group and crystal-structure determination.Acta Crystallogr. A Found. Adv.20157113810.1107/S205327331402637025537383
     [Google Scholar]
  15. SheldrickG.M. Crystal structure refinement with SHELXL.Acta Crystallogr. C Struct. Chem.20157113810.1107/S205322961402421825567568
     [Google Scholar]
  16. DemirtaşG. DegeN. İçbudakH. YurdakulÖ. BüyükgüngörO. Experimental and DFT Studies on Poly[di-μ3-acesulfamato-O,O:O′;O′:O,O-di-μ-acesulfamato-O,O; N-di-μ-aqua-dicalcium(II)] Complex.J. Inorg. Organomet. Polym. Mater.201222467167910.1007/s10904‑012‑9679‑7
     [Google Scholar]
  17. AlisirS.H. OzdemirN. BurgazE. DegeN. CanavarY.E. Fabrication and antimicrobial activity of poly(lactic acid) nanofibers containing firstly synthesized silver diclofenac complex with (2-methylimidazole) for wound dressing applications.Fibers Polym.202122102738274910.1007/s12221‑021‑0166‑z
     [Google Scholar]
  18. SpackmanM.A. JayatilakaD. Hirshfeld surface analysis.CrystEngComm2009111193210.1039/B818330A
     [Google Scholar]
  19. SpackmanP.R. TurnerM.J. McKinnonJ.J. WolffS.K. GrimwoodD.J. JayatilakaD. SpackmanM.A. CrystalExplorer : a program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals.J. Appl. Cryst.20215431006101110.1107/S160057672100291034188619
     [Google Scholar]
  20. KurbanovaM. AshfaqM. TahirM.N. MaharramovA. DegeN. KorogluA. Synthesis, crystal structure, supramolecular assembly exploration by hirshfeld surface analysis and computational study of 6-bromo-2-oxo- 2h-chromene-3-carbonitrile (bocc).J. Struct. Chem.202364230231310.1134/S0022476623020142
     [Google Scholar]
  21. Hamamci AlisirS. DegeN. TapramazR. Synthesis, crystal structures and characterizations of three new copper(II) complexes including anti-inflammatory diclofenac.Acta Crystallogr. C Struct. Chem.201975438839710.1107/S205322961900182730957784
     [Google Scholar]
  22. ElangovanN. SangeethaR. SowrirajanS. SaralaS. MuthuS. Computational Investigation on Structural and Reactive Sites (HOMO-LUMO, MEP, NBO, NPA, ELF, LOL, RDG) Identification, Pharmacokinetic (ADME) Properties and Molecular Docking Investigation of (E)-4-((4-chlorobenzylidene) amino) Benzene Sulfonamide Compound.Anal. Chem. Lett.2022121587610.1080/22297928.2021.1933588
     [Google Scholar]
  23. ElangovanN. ThomasR. SowrirajanS. IrfanA. Synthesis, spectral and quantum mechanical studies and molecular docking studies of Schiff base (E)2-hydroxy-5-(((4-(N-pyrimidin-2-yl)sulfamoyl)phenyl)imino)methyl benzoic acid from 5-formyl salicylic acid and sulfadiazine.J. Indian Chem. Soc.2021981010014410.1016/j.jics.2021.100144
     [Google Scholar]
  24. DegeN. IçbudakH. AdıyamanE. Bis(acesulfamato-κ 2O4,N)bis(3-methylpyridine)copper(II).Acta Crystallogr. C2006629m401m40310.1107/S010827010602788016954618
     [Google Scholar]
  25. AydemirE. KansizS. GumusM.K. GorobetsN.Y. DegeN. Crystal structure and Hirshfeld surface analysis of 7-eth{\}oxy 5 methyl 2 (pyridin 3 yl) 11,12 di{\ }hydro 5,11 methano{\ }[1,2,4]triazolo[1,5 {\it c}][1,3,5]benzoxadiazo{\}cine.Acta Crystallogr. Sect. E Struct. Rep. Online201874336737010.1107/S205698901800262129765725
     [Google Scholar]
  26. ElangovanN. GangadharappaB. ThomasR. IrfanA. Synthesis of a versatile Schiff base 4-((2-hydroxy-3,5-diiodobenzylidene)amino) benzenesulfonamide from 3,5-diiodosalicylaldehyde and sulfanilamide, structure, electronic properties, biological activity prediction and experimental antimicrobial properties.J. Mol. Struct.2022125013170010.1016/j.molstruc.2021.131700
     [Google Scholar]
  27. SowrirajanS. ElangovanN. AjithkumarG. SirajunnisaA. VenkatramanB.R. IbrahimM.M. MersalG.A.M. ThomasR. Synthesis, spectral, structural features, electronic properties, biological activities, computational, wave function properties, and molecular docking studies of (E)-4-(((pentafluorophenyl) methylene) amino)-N-(pyrimidin2-yl)benzenesulfonamide.J. Mol. Struct.2022126513347210.1016/j.molstruc.2022.133472
     [Google Scholar]
  28. LathaA. ElangovanN. ManojK.P. MaheswariV. BalachandranV. BalasubramaniK. SowrirajanS. ChandrasekarS. ThomasR. Synthesis, single crystal (XRD), spectral characterization, computational (DFT), quantum chemical modelling and anticancer activity of di(p-bromobenzyl) (dibromo) (1, 10-phenanthroline) tin (IV) complex.J. Indian Chem. Soc.2022991010071410.1016/j.jics.2022.100714
     [Google Scholar]
  29. Hamamci AlisirS. DegeN. A new antibacterial silver(I) complex incorporating 2,5-dimethylpyrazine and the anti-inflammatory diclofenac.Acta Crystallogr. C Struct. Chem.2016721294795110.1107/S205322961601700927918295
     [Google Scholar]
  30. IlmiR. KansızS. Al-RasbiN.K. DegeN. RaithbyP.R. KhanM.S. Towards white light emission from a hybrid thin film of a self-assembled ternary samarium( iii ) complex.New J. Chem.202044155673568310.1039/C9NJ06287D
     [Google Scholar]
  31. LathaA. ElangovanN. ManojK.P. KeerthiM. BalasubramaniK. SowrirajanS. ChandrasekarS. ThomasR. Synthesis, XRD, spectral, structural, quantum mechanical and anticancer studies of di(p-chlorobenzyl) (dibromo) (1, 10-phenanthroline) tin (IV) complex.J. Indian Chem. Soc.202299710054010.1016/j.jics.2022.100540
     [Google Scholar]
  32. AnthonyL.A. RajaramanD. SundararajanG. SureshM. NethajiP. JaganathanR. PoomaniK. Synthesis, crystal structure, Hirshfeld surface analysis, DFT, molecular docking and molecular dynamic simulation studies of (E)-2,6-bis(4-chlorophenyl)-3-methyl-4-(2-(2,4,6-trichlorophenyl)hydrazono)piperidine derivatives.J. Mol. Struct.2022126613348310.1016/j.molstruc.2022.13348335692554
     [Google Scholar]
  33. KanmazalpS.D. MacitM. DegeN. Hirshfeld surface, crystal structure and spectroscopic characterization of (E)-4-(diethylamino)-2-((4-phenoxyphenylimino)methyl)phenol with DFT studies.J. Mol. Struct.2019117918119110.1016/j.molstruc.2018.11.001
     [Google Scholar]
  34. MbaniA.L.O. YufanyiD.M. TabongC.D. HubertN.J. YuohA.C.B. PaboudamA.G. OndohA.M. Synthesis, crystal structure, DFT studies and Hirshfeld surface analysis of Manganese(II) and Cadmium(II) coordination polymers of 2-aminopyridine and dicyanamide.J. Mol. Struct.2022126113295610.1016/j.molstruc.2022.132956
     [Google Scholar]
  35. ÖztürkF. Structural characterization (XRD, FTIR) and magnetic studies of Cd(II)-Sulfamethoxazole-2,2′-bipyridine: DFT and Hirshfeld Surface Analysis.J. Mol. Struct.2023127113394510.1016/j.molstruc.2022.133945
     [Google Scholar]
  36. SenP. AtmacaG.Y. ErdogmusA. KanmazalpS.D. DegeN. YildizS.Z. Peripherally tetra-benzimidazole units-substituted zinc(II) phthalocyanines: Synthesis, characterization and investigation of photophysical and photochemical properties.J. Lumin.201819412313010.1016/j.jlumin.2017.10.022
     [Google Scholar]
  37. DemirS. CakmakS. DegeN. KutukH. OdabasogluM. KepekciR.A. A novel 3-acetoxy-2-methyl-N-(4-methoxyphenyl)benzamide: Molecular structural describe, antioxidant activity with use X-ray diffractions and DFT calculations.J. Mol. Struct.2015110058259110.1016/j.molstruc.2015.08.014
     [Google Scholar]
  38. WaniM.A. BelekarR.M. AthawaleS.A. WankhedeY.B. MuleyG.G. KakdeA.S. RaghuvanshiM.R. Energy transfer mechanism of Eu2+, Mn2+Doped lithium aluminate phosphor: Synthesis, Hirshfeld surface analysis and optical study.Mater. Chem. Phys.202229212679610.1016/j.matchemphys.2022.126796
     [Google Scholar]
  39. EvecenM. TanakH. TinmazF. DegeN. Özer İlhanİ. Experimental (XRD, IR and NMR) and theoretical investigations on 1-(2-nitrobenzoyl)3,5-bis(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole.J. Mol. Struct.2016112611712610.1016/j.molstruc.2016.01.069
     [Google Scholar]
  40. HernándezB. NareaP. CisternaJ. MaxwellL. CárdenasA. BritoI. DelgadoG.E. Synthesis, spectroscopy and crystal structure characterization, Hirshfeld surface analysis and energy framework calculations of 1-acetyl-5-(2-(methylthio) ethyl)-2-thioxoimidazolidin-4-one.J. Mol. Struct.2021124513107010.1016/j.molstruc.2021.131070
     [Google Scholar]
  41. IqbalY. HaroonM. AkhtarT. AshfaqM. TahirM.N. RasheedL. YousufM. ZiaM.A. Synthesis, spectroscopic characterization, single crystal XRD, Hirshfeld Surface analysis and theoretical studies (DFT) of 4-adamantyl-(2-(substitutedbenzylidene)hydrazinyl)thiazoles.J. Mol. Struct.2022126713362010.1016/j.molstruc.2022.133620
     [Google Scholar]
  42. DemirS. SarioğluA.O. GülerS. DegeN. SönmezM. Synthesis, crystal structure analysis, spectral IR, NMR UV–Vis investigations, NBO and NLO of 2-benzoyl-N-(4-chlorophenyl)-3-oxo-3-phenylpropanamide with use of X-ray diffractions studies along with DFT calculations.J. Mol. Struct.2016111831632410.1016/j.molstruc.2016.04.042
     [Google Scholar]
  43. KansızS. QadirA.M. DegeN. FaiziS.H. Two new copper (II) carboxylate complexes based on N,N,N′,N′-tetramethylethyleneamine: Synthesis, crystal structures, spectral properties, dft studies and hirshfeld surface analysis.J. Mol. Struct.2021123012991610.1016/j.molstruc.2021.129916
     [Google Scholar]
  44. GangaM. KalaivananC. SankaranK.R. Synthesis, SC-XRD, DFT Investigation and Hirshfeld Surface Analysis of 1-Neopentyl-2,4,5-Triphenyl-1H-Imidazole Derivatives.Polycycl. Aromat. Compd.202210.1080/10406638.2022.2038217
     [Google Scholar]
  45. MuslimM. AliA. NeogiI. DegeN. ShahidM. AhmadM. Facile synthesis, topological study, and adsorption properties of a novel Co (II)-based coordination polymer for adsorptive removal of methylene blue and methyl orange dyes.Polyhedron202121011551910.1016/j.poly.2021.115519
     [Google Scholar]
  46. KansızS. TolanA. AzamM. DegeN. AlamM. SertY. Al-ResayesS.I. İçbudakH. Acesulfame based Co(II) complex: Synthesis, structural investigations, solvatochromism, Hirshfeld surface analysis and molecular docking studies.Polyhedron202221811576210.1016/j.poly.2022.115762
     [Google Scholar]
  47. TamerÖ. DegeN. DemirtaşG. AvcıD. AtalayY. MacitM. AğarA.A. An experimental and theoretical study on the novel (Z)-1-((naphthalen-2-ylamino)methylene)naphthalen-2(1H)-one crystal.Spectrochim. Acta A Mol. Biomol. Spectrosc.2014117132310.1016/j.saa.2013.07.09823978793
     [Google Scholar]
  48. IlmiR. ZhangD. DutraJ.D.L. DegeN. ZhouL. WongW-Y. RaithbyP.R. KhanM.S. A tris β-diketonate europium(III) complex based OLED fabricated by thermal evaporation method displaying efficient bright red emission.Org. Electron.20219610621610.1016/j.orgel.2021.106216
     [Google Scholar]
  49. AkhileshwariP. KiranK.R. SridharM.A. SadashivaM.P. LokanathN.K. Synthesis, crystal structure characterization, Hirshfeld surface analysis, and Quantum chemical computations of Ethyl 5-(thiophene-2-carbonyl)thiazole-4-carboxylate.J. Mol. Struct.2021124213074710.1016/j.molstruc.2021.130747
     [Google Scholar]
  50. ManikandanA. DhanalakshmiM. GuganathanL. KokilaT. SanthamoorthyM. MarkkandanR. KimS.C. BalakrishnanC. Synthesis, structural characterization and Hirshfeld surface analysis of C H···O hydrogen-bonded supramolecular complexes of 18-crown-6 with imidazolinium derivatives.J. Mol. Struct.2022125413239510.1016/j.molstruc.2022.132395
     [Google Scholar]
  51. KansizS. DegeN. OzturkS. AkdemirN. TarcanE. ArslanhanA. SaifE. Crystal structure and Hirshfeld surface analysis of 2-methyl-3-nitro- N -[( E )-(5-nitrothiophen-2-yl)methylidene]aniline.Acta Crystallogr. E Crystallogr. Commun.202177213814110.1107/S205698902100052933614142
     [Google Scholar]
  52. HernándezB. Synthesis, crystal structure, Hirshfeld surface analysis, thermal, luminescent properties, and computational studies of the new triazole derivative 1-(5-methyl-1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)ethan-1-one.J. Mol. Struct.2022202213435310.1016/j.molstruc.2022.134353
     [Google Scholar]
  53. DenningtonR. KeithT. MillamJ. GaussView, Version 4.1. 2.Semichem Inc Shawnee Mission KS2007
     [Google Scholar]
  54. VishwanathT. AshishA. ShankarC.K.R. AmarK.D. Single-crystal XRD, Hirshfeld surfaces, 3D energy framework calculations, and DFT studies of 4,5-diphenyl-1,3,4-thiadiazole-2-thiolate: A mesoionic compound.J. Mol. Struct.2022126413329010.1016/j.molstruc.2022.133290
     [Google Scholar]
  55. FrischA. Gaussian 09, Revision B. 01.Gaussian, Inc.Wallingford USA.2009
     [Google Scholar]
  56. LondonF. About some properties and applications of molecular forces.J. Phys. Chem.193011222251
     [Google Scholar]
  57. StoneA.J. The Theory of Intermolecular Forces.OxfordClarendon Press199610.1093/oso/9780198558842.001.0001
     [Google Scholar]
  58. AskerovR.K. Synthesis, crystal structure, exploration of the supramolecular assembly through Hirshfeld surface analysis and bactericidal activity of the cadmium organometallic complexes obtained from the heterocyclic ligand.Resul. Chem.2022410060010.1016/j.rechem.2022.100600
     [Google Scholar]
  59. KhurshidA. SaeedA. ErbenM.F. HökelekT. JabeenE. DFT guided substitution effect on azomethine reactive center in newly synthesized Schiff base aromatic scaffolds; syntheses, characterization, single crystal XRD, Hirshfeld surface and crystal void analyses.J. Mol. Struct.2023127313421510.1016/j.molstruc.2022.134215
     [Google Scholar]
  60. Jone KirubavathyS. VelmuruganR. ParameswariK. ChitraS. Synthesis, characterization, single crystal XRD, in vitro antimicrobial and cytotoxicity study of tris(ethylenediamine)cobalt(III)chloride oxalate trihydrate.Arab. J. Chem.20191271581158610.1016/j.arabjc.2014.10.013
     [Google Scholar]
  61. PalakkeezhillamV.N.V. HaribabuJ. ManakkadanV. RasinP. VarugheseR.E. GayathriD. BhuvaneshN. EcheverriaC. SreekanthA. Synthesis, spectroscopic characterizations, single crystal X-ray analysis, DFT calculations, in vitro biological evaluation and in silico evaluation studies of thiosemicarbazones based 1,3,4-thiadiazoles.J. Mol. Struct.2023127313430910.1016/j.molstruc.2022.134309
     [Google Scholar]
/content/journals/cos/10.2174/0115701794309830240529042210
Loading
Structural Investigation and Hirshfeld Surface Analysis of 2-6-Dimethoxy-4-((2-Nitrophenylimin)Methyl) Phenol
Curr. Org. Synth. 22, 361 (2025); https://doi.org/10.2174/0115701794309830240529042210
/content/journals/cos/10.2174/0115701794309830240529042210
/content/journals/cos/10.2174/0115701794309830240529042210
Loading

Data & Media loading...


  • Article Type:     Research Article
Keyword(s): computational; DFT; hirshfeld surface analysis; single crystal; supramolecular chemistry; Synthesis

Most Cited Most Cited RSS feed

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test