Research Article. Ultrasonic studies on molecular interaction of substituted thiazolidines in acetone using pulse-echo technique

Transcription

1 Available online Journal of Chemical and Pharmaceutical Reearch, 2013, 5(11): Reearch Article I : CDE(UA) : JCPRC5 Ultraonic tudie on molecular interaction of ubtituted thiazolidine in acetone uing pule-echo technique Ahraf A Aly a*, Eam A. Ihak a, Amin Abd El Moneim b, Mohammed D Alenezy c,.. Abd El Aal d and L. Abd El Latif d a Chemitry Department, Faculty of cience, Al Jouf Univerity, akaka, Al Jouf, KA b Department of Baic cience, Education College, Univerity of Dammmam, KA c Phyic Department, Faculty of cience, Al Jouf Univerity, akaka, Al Jouf, KA d Ultraonic laboratory, ational intitute for tandard, Tera treet, 136 El-arem, El Giza, Egypt ABTRACT Velocitie of longitudinal ultraonic wave have been meaured at room temperature for ubtituted thiazolidine in acetone (w:v %) uing pule-echo technique. Data of the meaured ultraonic velocity and denity were ued to evaluate many acoutical and volumetric parameter, uch a pecific acoutic impedance, adiabatic compreibility, partial molal volume, intermolecular free length, apparent molal compreibility, relative aociation and alvation number. The change in thee parameter have been interpreted in term of acetone concentration. Reult howed that, the acoutical and volumetric parameter yielded valuable information about the behavior of acetone in the invetigated olution of thiazolidine. Key word: Thiazolidine, ultraonic velocity, adiabatic compreibility. ITRDUCTI It ha been noticed over the year that intereting biological activitie were aociated with thiazolidine. Recently application of thiazolidine were found in drug development for the treatment of allergie, [1] IV infection, [2] tumor, [3] bacterial and inflammation. [3,4] Aly et al have recently reported on the ynthei of variou elected thiazolidine of antibacterial and antioxidant activitie. [5,6] In the recent year, the ultraonic non-detructive puleecho technique ha been found to be one of the bet technique to characterize the acoutical propertie of material. The meaurement of the ultraonic velocity are helpful to interpreted olute-olvent, ionolvent interaction in aqueou and non aqueou medium. [7-9] Fumio et al [10] tudied the acoutical propertie of complex in water. It wa invetigated the acoutical propertie of four different drug in methanol and/or water and it wa drawn concluion from adiabatic compreibility. [11,12] Mehram et al alo tudied the different acoutical propertie of ome ubtituted pyrazoline in binary mixture acetone-water and oberved variation of ultraonic velocity with concentration. [13] In other ite, Palani meaured both ultraonic velocity and denity of amino acid in aqueou magneium acetate at contant temperature. [14] It wa found that the ion-dipole interaction mainly depend on ion ize and polarity of olvent. The trength of ion-dipole attraction i directly proportional to the ize of the ion, magnitude of dipole. owever that inverely proportional to the ditance between ion and molecule. [15] The acoutical and thermodynamic propertie of citric acid in water at different temperature. [16] Mihra et al have invetigated ultraonic velocity and denity in non aqueou olution of metal complex and evaluate acoutic propertie of metal complex. [17] Arvinthraj et al have determined the acoutic propertie for the mixture of amine with amide in benzene at 303K-313K. They alo determined thermodynamic parameter 13..K. [18] Thakur et al have tudied the different acoutical parameter of binary mixture of 1-propanol and water. [19] After review of literature urvey the detail tudy of ubtituted heterocyclic drug under identical et of experimental condition i till lacking. It wa thought of interet to tudy the acoutical propertie of propective thiazolidine drug under 762

2 uitable condition. Therefore, the goal of the preent work i to meaure the room temperature ultraonic velocity for ubtituted thiazolidine, prepared a reported in literature, [5,6] in acetone (w/v)% a a olvent uing pule-echo technique. The data of meaured velocity and denity will be ued to evaluate many acoutical and volumetric parameter, uch a the pecific acoutic impedance, adiabatic compreibility, intermolecular free length, apparent molal compreibility, relative aociation and alvation number. EXPERIMETAL ECTI The ubtituted thiazolidine, [5,6] are ued in the preent tudy. Acetone i ued for olution preparation of different drug. The denitie ( d ) of the invetigated olution were determined by uing pecific gravity bottle. The relative error in thee meaurement wa about ± 1x10-4 g/cm 3. The meaurement of ultraonic velocity ( U ) in each invetigated liquid ample wa carried out at room temperature and at 2 Mz frequency by uing pule- echo technique (GE model: U60). The elaped time between the initiation and the receipt of the pule wa determined. The velocity wa therefore obtained by dividing the round trip ditance by the elaped time. The temperature of the olution wa mentioned contant by circulating water through the double wall meauring cell made up of gla. imple combination of the meaured ultraonic velocity and denity allow the determination of the variou acoutic and volumetric propertie according to the following tandard relation: pecific acoutic impedance Z = d U (1) 1 Adiabatic compreibility β = (2) d U 1/ 2 Intermolecular free length L = Kβ (3) f where K i Jacobon contant, which i given at temperature T by the relation K = ( T )10. Acetone conc.(%) are expreed by ml: mg (acetone: mg) to give total of one hundred. Accordingly, high concentration of the compound i found, at 55% of it (45 ml of acetone). C 3 REULT AD DICUI Cl C 3 3 C 1a C Cl 1b C 1c C 3 C 2 C 3 C 1d 3 C 2 C C 1e C 3 C 2 C 2a C 3 Cl 2c C 3 2b Figure 1. tructure of elected thiazolidine 1a-e and 1a-c 763

3 Ultraonic parameter of elected thiazolidine 1a-e and 2a-c (Figure 1) were meaured e.g. denity ( d ) and ultraonic velocity ( U ), are lited in Table 1 for all olution under invetigation, beide the calculated value of adiabatic compreibility ( β ), partial molal volume ( f ), intermolecular free length ( L ), apparent molal compreibility ( f ), pecific acoutic impedance ( Z ), relative aociation ( R ), olvation number ( ). It i k een from the table that all the parameter are trongly dependent upon the concentration of acetone in the olution. It i well known that, the ultraonic wave travel more fater in a more dene material. Thi i true in cae of the invetigated olution a hown in Table 1. Figure 2 illutrate how the ultraonic velocity varie with the concentration of acetone in all olution under invetigation. The figure how clearly that, the ultraonic velocity decreae linearly with increaing concentration of acetone in the olution. The change in the ultraonic velocity can be explained on the bai of a model preented by Eyring and Kincaid [20] for ound propagation a follow. According to thi model, variation of ultraonic velocity in olution depend upon the increae or decreae of intermolecular free length after mixing the component. Generally, it i expected that the intermolecular free length and ultraonic velocity hould how a invere relation with each other. It ha been found that, increaing the concentration of the ubtituted heterocyclic compound in dioxane lead to an increae in the intermolecular free length and decreae in the meaured ultraonic velocity. The increae in the intermolecular free length to the greater force of interaction between olute and olvent by forming hydrogen bonding. [20] Thi i due to the ignificant interaction between ion and olvent molecule uggeting a tructure promoting behavior of the added electrolyte. Thi may alo indicate that decreae in number of free ion howing the occurrence of ionic aociation due to weak ion-ion interaction. In cae of the invetigated olution, the behavior of the intermolecular free length with the percentage of acetone i completely oppoite to that of the meaured ultraonic velocity. Thee reult prove that Eyring and Kincaid model [20] i valid for the invetigated olution. Equation (1) ugget that the acoutic impedance of material depend on two major parameter, which are the denity and ultraonic velocity. v A f n Figure. 2: Variation of ultraonic velocity with acetone concentration for the ubtituted thiazolidine 1a-e and 2a-c in acetone-water mixture. The olid line are drawn a a guide to the eye. ne intereting obervation in Table 1 i that, the meaured denity value change lightly with increaing the acetone concentration in all tudied olution. Thi ugget that ultraonic velocity i the controlled factor for etimating the acoutic impedance of thee olution. Thi ugget that ultraonic velocity i the controlled factor for etimating the acoutic impedance of thee olution. Thi explain why the acoutic impedance behave the ame trend a that of ultraonic velocity with acetone concentration. Generally, it i expected that the acoutic impedance 764

4 and adiabatic compreibility hould how oppoite behavior to each other. Thi i alo true in cae of the invetigated ytem a hown in Table 1. The decreae in the pecific acoutic impedance and an increae of adiabatic compreibility with the increae of percentage of acetone in the olution may be due to collection of olvent molecule around ion. Thi behavior indicate the exitence of weak ion-olvent interaction [21] and indicate that there i ignificant olute-olvent interaction. Table 1. Ultraonic velocity, denity, adiabatic compreibility and pecific acoutic impedance Intermolecular free length of olution with different percentage of acetone-water mixture. Acetone conc.(%) Ultraonic velocity(m/) Denity (Kg/m³) Adiabatic compreibility (x10-10 Kg/m 2 ) Intermolecular free length ( x10-11 m) Acoutic impedance ( x10 6 Kg/m²) 1a b c d e a b c C 2 C 3 2a C 3 Figure 3. uggeted hydrogen bond formation in compound 2a In Table 1, it i alo cleared that high intermolecular length wa appeared in 1d compared with other ubtituent, uggeted that increaing it hydrogen bond interaction in olution. It i well-known that biological activity of chemical compound depend on the preence of intermolecular hydrogen bond (IB). [22] Thu, it can be noted that compound 1d would how potentially high biological activity a compared with the other ubtituent due to the baicity pyridine moiety. [5] From Beide, it can be alo concluded that high dilution of the organic moiety (75% 765

5 acetone) increae with the intermolecular free length, o that more increaing of the hydrogen bond formation. Thu, it can be noted that compound 1d would how potentially high biological activity a compared with the other ubtitutent due to the baicity pyridine moiety. [5] Beide, it can be alo concluded that high dilution of the organic moiety (75% acetone) increae with the intramolecular free length, o that more increaing of the hydrogen bond formation. It i obviouly noted that compound 2a-c contain three oxygen atom a electronegative element that enable to hydrogen bond formation (e.g. compound 2a, Figure 3) with the olvent and conequently indicate high interamolecular length compared with thoe in 1a-e at more dilution. It i known that the ultraonic ound wave caue ocillation in preure but the ocillation are fat enough that heat can't move from compreed region to rarified region in order to keep the temperature contant. Before the heat can be conducted away from the compreed region the compreion ha moved on o that ound propagation i adiabatic. Although tatic meaurement have been ued for thi purpoe, the obervation indicated that meaurement of protein dynamic are effectively a more enitive method of determining the condition under which protein are mot table. [23] Accordingly, meaurement of adiabatic compreibility, herein, would give information about the tability of thiazole moiety a a propective drug againt degradation. Moreover, and from Table-1 it i noted that generally, denity and ultraonic velocity increae with increae in molar olution. The increae in velocity i due to the decreae in adiabatic compreibility of the liquid olution. The adiabatic compreibility are the deciding factor of the ultraonic velocity in the liquid olution which directly relate with the anti-bacterial activity of that compound. More olution concentration of olution more active i the compound toward bacteria hence a the concentration increae activity increae which relate with the effect of adiabatic compreibility of the compound. ence adiabatic compreibility value i inverely proportional to the molar olution concentration. CCLUI In concluion, acoutical and volumetric parameter uing ultraonic echo technique can give u valuable information about the behavior of thiazolidine in olution of the olute-olvent interaction. Therefore much more tudie are required to apply the aforeaid tudy to variou heterocycle in order to tudy their tability in olution and to introduce information about their tabilitie in olution to be ued a potentially biological active compound. Acknowledgement The author expre their gratitude to Al Jouf Univerity, KA for the reearch fund and it upport of thi invetigation. REFERECE [1] L. Racane, V. Tralic-Kulenovic, L.F. Jakic, D. W. Boykin, G. Karminki-Zamola, eterocycle, 2001, 55, [2] A. A. Aly, A. B. Brown, M. Abdel-Aziz, G. El-Din A. A. Abuo-Rahma, M. F. Radwan, M. Ramadan, A. M. Gamal-Eldeen J. eterocycl. Chem. 2012, 49, [3] B.. olla, K. V. Malini, B.. Rao, B. K. arojini,.. Kumari Eur. J. Med. Chem., 2003, 38, [4]. C. Deai, V. V. Johi, K. M. Rajpara,. V. Vaghani,. M. atodiya J. Fluorine Chem., 2012, 142, [5] A. A Aly, E. A. Ihak, T. El Malah, A. B. Brown, W. M. Elayat, J. eterocycl. Chem., 2013 (ubmitted). [6] A. A Aly, E. A. Ihak, A. B. Brown, W. M. Elayat, J. ulf. Chem (ubmitted) [7]. Baluja,. za, Fluid phae equlibria, 2005, 200, [8] M. K. Rawat, angeeta, Ind. J. pure Appl. Phy. 2008, 46, [9] A. Ali, A. K. ain, Acoutic Lett. 1996, 19, [10]. gawa,. J. Murakami J. olution. Chem. 1987, 16, [11] F. Kawaizumi, K. Matumoto,. omura J. Phy. Chem. 1983, 87, [12] D. V. Jahagirdar, B. R. Arbad,. R. Mirgane, M. K. Lande, A. G. hankarvar J.Molecular Liq. 1998, 75, [13] Y. K. Mehram, M. L. arwade Acta Ciencia Indica 2001, XXVII.C, [14] R. Palani,. aravanan Reearch J. Phy. 2008, 2, [15] V. K. yal, A. Chauhan,. Chauhan J. Pure Ultraound. 2005, 27, [16] A. Tadkalkar, P. Pawar, G. K. Bichile J. Chem. Pharm. Re. 2011, 3, [17] A. P. Mihra, D. K. Mihra, J. Chem. Pharm. Re. 2011, 3, [18] M. Arvinthraj,. Venktean, D. Meera, J. Chem. Pharm. Re, 2011, 3, [19]. K. Thakur,.Chauhan, J. Chem. Pharm. Re., 2011, 3, [20]. Eyring, J. F. Kincaud, J. Chem. Phy, 1938, 6, [21] J. D. Pandey, A hukla, R. D. Rai, K. J. Mihra, J. Chem. Eng. Data.,1989, 34, [22] Intermolecular Interaction: From Diatomic to Biopolymer, B. Pullman, Ed., ew York,

6 [23] J. D. Ramey, M. L. Gill, T. J. Kamerzell, E.. Price,. B. Johi,. M. Bihop, C.. liver, C. R. Middaugh, J Pharm ci. 2009, 98,