Advertisement

Colloid and Polymer Science

, Volume 297, Issue 11–12, pp 1519–1527 | Cite as

Interaction of ninhydrin with zinc(II) complex of tryptophan in the three dicationic gemini surfactants

  • Malik Abdul Rub
  • Dileep KumarEmail author
Original Contribution
First Online:
  • 63 Downloads

Abstract

Present work concerns with the interaction of ninhydrin with zinc(II) complex of tryptophan ([Zn(II)-Trp]+) in the three dicationic gemini surfactant systems. To record critical micellar concentration (CMC) and absorbance, we have used Systronics conductivity meter and UV-visible spectrophotometer, respectively. Experiment opens up the fractional- and first-order paths in ninhydrin and complex, respectively. Gemini micellar medium is found more superior over aqueous medium. Rate constant (kψ) vs. [gemini] plot shows the unusual role of geminis on kψ. kψ increases with gemini concentration (at concentrations lower than the CMC, part I) and leveling-off regions obtain (concentration up to 400 × 10−5 mol dm−3, part II). Characteristics of part I and part II are just the same as that of conventional surfactant. Later, gemini produces a third region of increasing kψ at higher concentrations ([gemini] > 400 × 10−5 mol dm−3, part III). Detail and systematic elucidation about the effect of surfactants are mentioned and discussed in the text. Binding constants (KS for [Zn(II)-Trp]+ and KN for ninhydrin) and rate constant (km in geminis) were determined by nonlinear least squares regression technique. The kinetic results acquired can reasonably be interpreted by pseudo-phase model of surfactant micelles.

Keywords

Gemini surfactants Interfaces CMC [Zn(II)-Trp]+ Ninhydrin 
This is a preview of subscription content, log in to check access.

Notes

Acknowledgments

This project was funded by the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, under grant No. (DF-071-130-1441). The authors, therefore, gratefully acknowledge DSR technical and financial support.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

References

  1. 1.
    Rosen MJ (2004) Surfactants and interfacial phenomena3rd edn. John Wiley & Sons, New YorkGoogle Scholar
  2. 2.
    Kumar D, Rub MA (2017) Effect of anionic surfactant and temperature on micellization behavior of promethazine hydrochloride drug in absence and presence of urea. J Mol Liq 238:389–396Google Scholar
  3. 3.
    Kumar D, Hidayathulla S, Rub MA (2018) Association behavior of a mixed system of the antidepressant drug imipramine hydrochloride and dioctyl sulfosuccinate sodium salt: effect of temperature and salt. J Mol Liq 271:254–264Google Scholar
  4. 4.
    Sun Y, Xu X, Qin M, Pang N, Wang G, Zhuang L (2019) Dodecyl sulfate-based anionic surface-active ionic liquids: synthesis, surface properties, and interaction with gelatin. Colloid Polym Sci 297:571–586Google Scholar
  5. 5.
    Jiang P, Zhang L, Tang D, Li L, Ge J, Zhang G, Pei H (2019) Effect of nano-SiO2 and surfactants on the oil-water interfacial properties. Colloid Polym Sci 297: 903-915Google Scholar
  6. 6.
    Holland PM (1992) Mixed surfactants systems, Holland PM, Rubingh DN (Eds.), ACS Symposium Series 501. American Chemical Society, Washington, DCGoogle Scholar
  7. 7.
    Amin MR, Mahbub S, Molla MR, Alam MM, Hossain MF, Rana S, Rub MA, Hoque MA, Kumar D (2019) Phase separation and thermodynamic behavior of Triton X-100 in occurrence of levofloxacin hemihydrates: influence of additives. J Chem Eng Data 64:2750–2758Google Scholar
  8. 8.
    Ren ZH, Luo Y (2013) Dynamic interfacial tension behavior of alkyl amino sulfonate in crude oil-brine system. Tenside Surfactant Deterg 50:369–375Google Scholar
  9. 9.
    Gecol H, Scamehorn JF, Christian SD, Riddell FE (2003) Use of surfactants to remove solvent-based inks from plastic films. Colloid Polym Sci 281:1172–1177Google Scholar
  10. 10.
    Kumar D, Rub MA (2018) Interaction of ninhydrin with chromium-glycylglycine complex in the presence of dimeric gemini surfactants. J Mol Liq 250:329–334Google Scholar
  11. 11.
    Nakahara H, Nishino A, Tanaka A, Fujita Y, Shibata O (2019) Interfacial behavior of gemini surfactants with different spacer lengths in aqueous medium. Colloid Polym Sci 297:183–189Google Scholar
  12. 12.
    Bhardwaj P, Kamil M, Panda M (2018) Surfactant-polymer interaction: effect of hydroxypropylmethyl cellulose on the surface and solution properties of gemini surfactants. Colloid Polym Sci 296:1879–1889Google Scholar
  13. 13.
    Kumar D, Rub MA (2018) Synthesis and characterization of dicationic gemini surfactant micelles and their effect on the rate of ninhydrin–copper-peptide complex reaction. Tenside Surfactant Deterg 55:78–84Google Scholar
  14. 14.
    Zana R, Talmon Y (1993) Dependence of aggregate morphology on structure of dimeric surfactants. Nature 362:228–230Google Scholar
  15. 15.
    Lisa K, Marcel CP, Van E, Olle S (2009) Compaction of DNA by gemini surfactants: effects of surfactant architecture. J Colloid Interface Sci 252:290–296Google Scholar
  16. 16.
    Kumar D, Rub MA (2019) Kinetic study of ninhydrin with chromium(III)-glycylleucine in aqueous–alkanediyl-a,ωbis(dimethylcetylammonium bromide) gemini surfactants. J Phys Org Chem 32:e3946Google Scholar
  17. 17.
    Kumar D, Rub MA, Azum N, Asiri AM (2018) Mixed micellization study of ibuprofen (sodium salt) and cationic surfactant (conventional as well as gemini). J Phys Org Chem 31:e3730Google Scholar
  18. 18.
    Xia J, Zana R (2004) Gemini surfactants: synthesis, interfacial and solution-phase behavior, and applications. Marcel Dekker Inc., New YorkGoogle Scholar
  19. 19.
    Singh V, Tyagi R (2017) Physicochemical properties and effect of organic and inorganic electrolytes on surface properties of C12 and C16 alcohol-based bis-sulfosuccinate anionic gemini surfactants. Colloid Polym Sci 295:601–611Google Scholar
  20. 20.
    Khossravi D (1997) Drug-surfactant interactions: effect on transport properties. Int J Pharm 155:179–190Google Scholar
  21. 21.
    Kumar D, Azum N, Rub MA, Asiri AM (2018) Aggregation behavior of sodium salt of ibuprofen with conventional and gemini surfactant. J Mol Liq 262:86–96Google Scholar
  22. 22.
    Friedman F (2004) Applications of the ninhydrin reaction for analysis of amino acids peptides, and proteins to agricultural and biomedical sciences. J Agric Food Chem 52:385–406 (and references cited therein)PubMedGoogle Scholar
  23. 23.
    Joullie MM, Thompson TR, Nemeroff NH (1991) Ninhydrin and ninhydrin analogs. Syntheses and applications. Tetrahedron 47:8791–8830Google Scholar
  24. 24.
    Khan IA, Bano M, Kabir-ud-Din (2010) Micellar and solvent effects on the rate of reaction between l-tyrosine and ninhydrin. J Dispers Sci Technol 31:177–182Google Scholar
  25. 25.
    Kabir-ud-Din BM, Khan IA (2002) Reaction between l-glutamic acid and ninhydrin: role of organic solvents and CTAB micelles. J Surf Sci Technol 18:113–128Google Scholar
  26. 26.
    Kabir-ud-Din SJKJ, Kumar S, Rafiquee MZA, Khan Z (2000) Effect of cationic micelles on the kinetics of interaction of ninhydrin with l-leucine and l-phenylalanine. J Colloid Interace Sci 213:20–28Google Scholar
  27. 27.
    El-Sadek BM (2011) Synthesis of selected gemini surfactants: surface, biological activity, and corrosion efficiency against hydrochloric medium. Der Chemica Sin 2:125–137Google Scholar
  28. 28.
    Singh V, Tyagi R (2016) Steady-state fluorescence investigations of aqueous binary mixtures of myristyl alcohol based bissulfosuccinate anionic gemini surfactant and effect of different conventional surfactants therein. J Dispers Sci Technol 38: 265-271Google Scholar
  29. 29.
    Azum N, Asiri AM, Rub MA, Khan AAP, Khan A, Kumar D, Al-Youbi AO (2013) Mixed micellization of gemini surfactant with nonionic surfactant in aqueous media: a fluorometric study. Colloid J 75:235–240Google Scholar
  30. 30.
    De S, Aswal VK, Goyal PS, Bhattacharya S (1996) Role of spacer chain length in dimeric micellar organization. Small angle neutron scattering and fluorescence studies. J Phys Chem 100:11664–11671Google Scholar
  31. 31.
    Sharma KS, Rodgers C, Palepu RM, Rakshit AK (2003) Studies of mixed surfactant solutions of cationic dimeric (gemini) surfactant with nonionic surfactant C12E6 in aqueous medium. J Colloid Interface Sci 268:482–488PubMedGoogle Scholar
  32. 32.
    Kabir-ud-Din, Fatma W, Khatoon S, Khan ZA, Naqvi A.Z. (2008) Surface and solution properties of alkanediyl-α,ω-bis(dimethylcetylammonium bromide) gemini surfactants in the presence of additives. J Chem Eng Data 53:2291–2300Google Scholar
  33. 33.
    Kabir-ud-Din, Fatma W, Khan ZA, Dar AA (2007) 1H NMR and viscometric studies on cationic gemini surfactants in presence of aromatic acids and salts. J Phys Chem B 111:8860–8867PubMedGoogle Scholar
  34. 34.
    Connell GE, Dixon GH, Hanes CS (1955) Quantitative chromatographic methods for the study of enzymic transpeptidation reactions. Can J Biochem Physiol 33:416–427PubMedGoogle Scholar
  35. 35.
    Kalyankar GD, Snell EE (1957) Differentiation of α-amino-acids and amines by non-enzymatic transamination on paper chromatograms. Nature 180:1069–1070PubMedGoogle Scholar
  36. 36.
    McCaldin DJ (1960) The chemistry of ninhydrin. Chem Rev 60:39–51Google Scholar
  37. 37.
    MacFadyen DA, Fowler N (1950) On the mechanism of the reaction of ninhydrin with α-amino acids: II. A spectrophotometric study of hydrindantin reactions. J Biol Chem 186:13–22PubMedGoogle Scholar
  38. 38.
    Schonberg A, Moubasher R (1952) The Strecker degradation of α-amino acids. Chem Rev 50:261–277Google Scholar
  39. 39.
    Kabir-ud-Din BM, Khan IA (2003) Kinetics and mechanism of the ninhydrin reaction with dl-methionine in the absence and presence of organic solvents. Ind J Chem B 42:1132–1136Google Scholar
  40. 40.
    Kabir-ud-Din SJKJ, Kumar S, Khan Z (2000) Effect of cationic surfactants on the addition-elimination type interaction between aspartic acid and ninhydrin. Colloids Surf A Physicochem Eng Asp 168:241–250Google Scholar
  41. 41.
    Kabir-ud-Din FW, Khan Z (2006) Micelle-catalyzed reaction of ninhydrin with dl-valine in the absence and presence of organic solvents. Int J Chem Kinet 38:634–642Google Scholar
  42. 42.
    Kabir-ud-Din SJKJ, Kumar S, Khan Z (2000) Micellar and salts effect on Ruhemann’s purple formation between l-lysine and ninhydrin. Ind J Chem A 39:1019–1023Google Scholar
  43. 43.
    Brash JL, Horbett TA (1995) Proteins at interfaces II: Fundamentals and applications, vol 602. American Chemical Society, Washington, DCGoogle Scholar
  44. 44.
    Sonesson AW, Blom H, Hassler K, Elofsson UM, Callisen TH, Widengren J, Brismar H (2008) Protein-surfactant interactions at hydrophobic interfaces studied with total internal reflection fluorescence correlation spectroscopy (TIR-FCS). J Colloid Interface Sci 317:449–457PubMedGoogle Scholar
  45. 45.
    Otsuka Y, Ito A, Takeuchi M, Tanaka H (2019) Effect of amino acid on calcium phosphate phase transformation: attenuated total reflectance-infrared spectroscopy and chemometrics. Colloid Polym Sci 297:155–163Google Scholar
  46. 46.
    Zana R, Benrraou M, Rueff, R (1991) Alkanediyl-α,ω-bis(dimethylalkylammoniumbromide) surfactants. 1. Effect of the spacer chain length on the critical micelle concentration and micelle ionization degree. Langmuir 7:1072–1075.Google Scholar
  47. 47.
    Karaborni S, Esselink K, Hilbers PAJ, Smit B, Karthauser J, van Os NM, Zana R (1994) Simulating the self-assembly of gemini (dimeric) surfactants. Science 266:254–256PubMedGoogle Scholar
  48. 48.
    Mahbub S, Rub MA, Hoque MA, Khan MA, Kumar D (2019) Micellization behavior of cationic and anionic surfactant mixtures at different temperatures: effect of sodium carbonate and sodium phosphate salts. J Phys Org Chem 32: e3967Google Scholar
  49. 49.
    Kumar D, Rub MA (2017) Kinetic study of nickel-glycylglycine with ninhydrin in alkanediyl-α,ω-gemini (m-s-m type) surfactant system. J Mol Liq 240:253–257Google Scholar
  50. 50.
    Akram M, Kumar D, Kabir-ud-Din (2013) Zinc dipeptide complex ([Zn(II)-Gly-Tyr]+)–ninhydrin reaction in presence of gemini surfactants: a kinetic study. J Mol Liq 188:61–66Google Scholar
  51. 51.
    Akram M, Kumar D, Kabir-ud-Din (2013) Influence of cationic gemini and conventional CTAB on the interaction of [Cr(III)-Gly-Tyr]2+ complex with ninhydrin. Colloids Surf A Physicochem Eng Asp 428:92–99Google Scholar
  52. 52.
    Kumar D, Rub MA (2019) Role of cetyltrimethylammonium bromide (CTAB) surfactant micelles on kinetics of [Zn(II)-Gly-Leu]+ and ninhydrin. J Mol Liq 274:639–645Google Scholar
  53. 53.
    Kumar D, Rub MA (2018) Catalytic role of 16-s-16 micelles on condensation reaction of ninhydrin and metal-dipeptide complex. J Phys Org Chem 32:e3918Google Scholar
  54. 54.
    Menger FM, Portnoy CE (1967) Chemistry of reactions proceeding inside molecular aggregates. J Am Chem Soc 89:4698–4703Google Scholar
  55. 55.
    Bunton CA (1979) Reaction kinetics in aqueous surfactant solutions. Catal Rev Sci Eng 20:1–56Google Scholar
  56. 56.
    Cerichelli G, Mancini G, Luchetti L, Savelli G, Bunton CA (1994) Surfactant effects upon cyclization of o-(.omega.-haloalkoxy)phenoxide ions. The role of premicellar assemblies. Langmuir 10:3982–3987Google Scholar
  57. 57.
    Zhang Y, Li X, Liu J, Zeng X (2002) Micellar catalysis of composite reactions—the effect of SDS micelles and premicelles on the alkaline fading of crystal violet and malachite green. J Dispers Sci Technol 23:473–481Google Scholar
  58. 58.
    Khan MN (2006) Micellar catalysis; surfactant science series, vol 133. CRC Press, New YorkGoogle Scholar
  59. 59.
    Romsted LS (1984) Surfactants in solution, Mittal KL, Lindman B (Eds.), vol. 2. Plenum Press, New YorkGoogle Scholar
  60. 60.
    Savelli G, Germani R, Brinchi L (2001) Reactions and synthesis in surfactant systems, Surfactant science series, Texter J (Ed.), vol. 100. Marcel Dekker, New YorkGoogle Scholar
  61. 61.
    Brinchi L, Germani R, Goracci L, Savelli G, Bunton CA (2002) Decarboxylation and dephosphorylation in new gemini surfactants. Changes in aggregate structures. Langmuir 18:7821–7825Google Scholar
  62. 62.
    Rub MA, Kumar D, Azum N, Khan F, Asiri AM (2014) Study of the interaction between promazine hydrochloride and surfactant (conventional/gemini) mixtures at different temperatures. J Solut Chem 43:930–949Google Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Chemistry Department, Faculty of ScienceKing Abdulaziz UniversityJeddahSaudi Arabia
  2. 2.Division of Computational Physics, Institute for Computational ScienceTon Duc Thang UniversityHo Chi Minh CityVietnam
  3. 3.Faculty of Applied SciencesTon Duc Thang UniversityHo Chi Minh CityVietnam

Personalised recommendations

Cite article

Buy options