A Low Temperature Infrared Study on the Association of Thiols with Pyridine and Triethylamine

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1 Canadian Journal of Chemistry Published by THE NATIONAL RESEARCH COUNCIL OF CANADA Journal canadien de chimie PubW par LE CONSEIL NATIONAL DE RECHERCHES DU CANADA Volume 51 Number 7 April 1, 1973 Volume 51 numcro 7 1 avril 1973 A Low Temperature Infrared Study on the Association of Thiols with Pyridine and Triethylamine R. BICCA DE ALENCASTRO' AND C. SANDORFY DPpartemerzt de Ckimie, Universite' de Mot~treal, Morztre'al, Q~zPbec Received September 20, 1972 The infrared spectra of solutions containing propane-1-thiol or benzenethiol as proton donors, and pyridine or triethylamine as proton acceptors were measured down to about "C. The dependence of hydrogen bond formation on concentration and temperature was studied at the fundamental and overtone region of the S-H stretching vibration. The predominant species is found to be a 1 :1 S-H---N type complex. In addition, evidence was found for the existence of more highly associated species at low temperatures. Thiol-thiol S-H---n type hydrogen bonds are also present in the case of benzenethiol-pyridine mixtures. Les spectres infrarouges de solutions contenant du propanethiol-1 ou du benzenethiol comme donneurs de proton et de la pyridine OII de la triethylamine comme accepteurs de proton ont 8tB mesur6s a des temperatures allant de 20 "C B "C. Les effets de la concentration en base d'une part et de la temperature d'autre part sur la formation de la liaison hydrogene, ont 6t6 Btudits aux niveaux de la fondamentale et de la premitrre harmonique de la vibration de valence du groupement S-H. L'espece predominante est un complexe 1 :1 de type S-H---N. D'autre part, I'existence d'espkces plus assocites a etc mise en evidence aux temperatures les plus basses. Des liaisons hydrogene de type S-H---n autoassociies ont kt6 trouvees dans les melanges benztnethiol-pyridine. Can. J. Chern.. 51, 985 (1973) Introduction In a previous publication (1) we studied the self-association of both aliphatic and aromatic thiols in solution at low temperatures. Although the S-H---S hydrogen bonds formed are relatively weak, the existence of two or three differently associated species could be ascertained in most cases. As a second step in the study of the hydrogen bonds formed by S-H groups, we have examined some systems in which stronger bonds are expected. In the present paper we deal with S-H---N type bonds. Solutions of mercaptans in organic nitrogen bases are known to undergo both self-association 'Brazil-Canada exchange fellow. On leave of absence from Instituto de Quimica, Universidade Federal de Rio de Janeiro, Rio de Janeiro, Brazil. and association with the proton accepting solvent molecules. As early as in 1940, Gordy and Stanford (2) studied the variation of the infrared spectrum, in the region of the S-H stretching vibration, when mercaptans are dissolved in solvents such as pyridine, aniline, or benzylamine, and attributed these changes to association of the S-H---N type. Bulanin, Denisov, and Pushkina (3) observed association between propane-1-thiol and triethylamine. N.m.r. and U.V. studies (4, 5) confirmed this, and suggested that these complexes were of the 1 : 1 type. We have studied the association of propane-lthiol and benzenethiol with pyridine and triethylamine as proton acceptors over a wide temperature range, and have measured the fundamentals as well as the overtones of the S-H stretching vibration. The solvent used was

2 986 CAN. J. CHEM. VOL. 51, 1973 CC1,F (Freon 11) which enabled us to work at temperatures down to OC. We hoped to be able to follow the changing pattern of association with temperature, and to identify the bands due to the complexes formed between the thiols and the bases. Experimental The fundamentals were measured on a Perkin-Elmer Model 621 spectrometer and the overtones on a Cary 17 instrument. In the fundamental region, we used a 0.9 mm cell with silver bromide windows for low temperatures, and commercial 1.0 and 0.1 mm sodium chloride cells for room temperature spectra. A 1 cm quartz cell was used for the overtone region. More details of the experimental techniques are given elsewhere (6). Temperatures were measured with a copper-constantan thermocouple. CC13F (Freon 11) obtained from the E.I. Dupont de Nemours of Canada Co., was distilled and kept over phosphorus pentoxide. Spectrograde quality carbon tetrachloride from Anachemia Chems. Ltd., Montreal, was dried on molecular sieves of the type 4A. The mercaptans were the same as those used in our previous work (1). Pyridine, a spectroquality reagent from the Matheson, Coleman, and Bell Co., was treated with KOH pellets for at least 24 h before distillation. Triethylamine, from the same company, was dried over CaS04, and distilled. None of the i.r. spectra of these bases showed water absorption. All solutions were prepared gravimetrically in a drybox filled with nitrogen to avoid oxidation or moisture absorption. The concentrations were not corrected for solvent contraction since intensities measured at different temperatures were not compared. The correction should not exceed 15% at "C in any case. All curves were corrected for solvent absorption. Figures 1 and 4 show the spectrum of the thiol in an inert solvent, the spectrum of the base in the same solvent, the spectrum of the thiol-base mixture, and the spectrum of the mixture, obtained by subtracting the absorption of the base. In the other figures only the first and the last are shown. The solutions were used immediately after preparation. After 24 h, ternary solutions of mercaptans and triethylamine in CC13F, and solutions of mercaptans in triethylamine give a white crystalline precipitate. This solid shows (in Nujol) a band between 2650 and 2700 cm-', characteristic of the NH+ absorption (for a discussion on quaternary ammonium salts see ref. 7). After being in contact with the silver bromide windows of the low temperature cells for several hours, the pyridine solutions gave a white solid deposit, soluble in acetone, which is probably a silver-pyridine complex. This deposit, however, showed no appreciable absorption in our spectral region. Results and Discussion Figures 1 and 2 show the effect of temperature and pyridine concentration on the spectrum of the complex between propane-1-thiol and pyridine. The maximum of the S-H---N band is near 2520 cm-l, at room temperature, and at u (cni') FIG. 1. The infrared spectrum ( cm-') of (-), a 0.98 M solution of propane-i-thiol in CC1,F; (---), a 2.86 M solution of pyridine in CC1,F; (-..-). a mixture of 0.98 M propane-i-thiol and 2.86 M pyridine in CC1,F; (-.-), a mixture of 0.98 M propane-i-thiol and 2.86 M pyridine in CC1,F with the absorption due to pyridine subtracted. (a) 20 "C; (b) "C. Vertical axis: 111 log Io/I in cm-' units. FIG. 2. The infrared spectrum ( cm-') of (a) 5.92 M; (b) 1.43 M solutions of propane-1-thiol (-) in CCI, and (-.-) in pyridine, at 20 "C with the absorption due to pyridine subtracted cm-l, at "C. The increased haliwidth seems to indicate that this band is actually due to more than one species. The band center must receive most of its intensity from the 1: 1 complex, that is, from S-H---N type bonds. On the high frequency side, both free and S-H ---S bonds can contribute to the intensity. On

3 BICCA DE ALENCASTRO AND SANDORFY: ASSOC[ATION OF THIOLS 987 FIG. 3. The infrared spectrum ( cm-') of ((I) 1.43 M; (6) 2.75 M; (c) 5.92 M solutions of propane-1- thiol (-) in CCI, and (-.-) in pyridine, at 20 "C with the absorption due to pyridine subtracted. Vertical axis: l/l log Io/I in cm-' units. the low frequency side, S-H---N type bonds of more highly nssociated species of the type S-H---S-H---N come in. Of course, the S-H---S group of the latter may contribute to the intensity on the high frequency side. The breadth and the intensitv increase of this band on its low frequency side as the temperature decreases, can be taken as an indication of the presence of such more highly associated complexes. - 'E U - Figures 3 and 4 show that, at the first overtone, the free band is present up to a thiol-pyridine ratio of 1 :7, (Fig. 3a) but is absent at higher pyridine concentrations. In all cases, however, the presence of pyridine decreases the intensity of the free band showing that S-H---N type association occurs. At lower temperatures and higher concentrations a broad band appears near 4900 cm-'. This must be the S-H---N band of the 1 : 1 complex. As we are limited by the crystallization temperature of pyridine and by the stronger bands near 4800 cm-' of pyridine (still strong enough in pyridine-d, to prevent concentration or temperature studies) we cannot observe the band of the more associated species at the overtone level. Studies in solution of inert solvents at lower tem~eratures are not possible because we are dealing with very weak bands. Figures 5 and 6 show the results we obtained for the benzenethiol-pyridine complex. This is known to be a 1 : 1 complex at room temperature (4). The spectrum shows, at 20 "C, a broad and rather symmetrical band centered near 2430 cm-'. This spectrum yields two interesting results. First, the band is very broad. Secondly, even with a 3:l excess of pyridine to thiol the band near 2572 cm-' still persists. The latter band is assigned to thiol-thiol S-H---7c type hydrogen bonds. The free band is weaker and cannot be seen in the spectrum. However, it can be observed for similar concentrations at the overtone (see below). At low temperature (- 101 "C) the broad band is asymmetrical on the lower frequency side. This is again probably FIG. 4. The infrared spectrum ( cm-i) of (-), a 5.74 M solution of propane-i-thiol in CC13F; (---), a 5.54 M solution of pyridine in CCI3F; (-..-), a mixture of 5.74 M propane-1-thiol and 5.54 M pyridine; (-.-), a mixture of 5.74 M propane-1-thiol and 5.54 M pyridine with the absorption due to pyridine subtracted. (a) 20 "C; (6) -20 "C. Vertical axis: 111 log Io/I in cm-i units.

4 988 CAN. J. CHEM. \ 'OL. 51, 1973 FIG. 5. The infrared spectrum ( cm-') of (-), a 0.27 M solution of benzenethiol in CC1,F; (-.-), a mixture of 0.27 M benzenethiol and 0.92 M pyridine in CC1,F. (a) 20 "C; (b) "C. The absorption due to pyridine is subtracted. Vertical axis: 111 log loll in cm-' units. ""t b, FIG. 6. The infrared spectrum ( cm-') of (a) 0.68 M and (b) 2.54 M solutions of benzenethiol (-) in CC1,F and (-.-) in pyridine, at 20 OC with the absorption due to pyridine subtracted. Vertical axis: 111 log Io/I in crn-' units divided by ten. due to a more associated species. Another interesting observation is the breaking of some of the self-associated S-H---x bands at low temperatures. At the first overtone level (Fig. 7) the spectra are less conclusive due to the severe overlap with the much stronger bands of pyridine near 4800 cm-l. Nevertheless some interesting remarks can be made. The "free" band loses intensity when the concentration of pyridine is raised and is shifted toward lower frequencies. A band, partially overlapped by pyridine absorption, can be seen at lower frequencies and should be ascribed to the S-H---N vibration of the 1 :1 complex. As we showed in our previous work (1) the "free" band of benzenethiol is due, at the overtone level, to the actual free band and to the selfassociated S-H---x type band. This is further confirmed in the present work by concentration studies at the overtone level (compare (a), (b), and (c) of Fig. 7). In the presence of pyridine we expect that the S-H---N complexes are formed by preferentially using the free S-H groups still present, rather than breaking existing weaker complexes. In a dilute solution of an inert solvent, the benzenethiol free band is expected to predominate over the S-H---x type band, but the reverse is true if the solvent is pyridine. Increasing the concentration of benzenethiol should favor the S-H---x bonds in both solvents. This is translated by two effects in the spectra of Fig. 7. First, the apparent maximum of the overlapping free S-H and S-H---x bands is at higher frequencies when pyridine is absent. Secondly, the difference between these two frequencies is greater for dilute solutions of benzenethiol. In addition, the S-H---x type band is seen to persist for similar concentrations (compare Figs. 6(b) and 7(b)) at the fundamentals. We therefore think that the band which remains at higher pyridine concentrations, near 5050 cm-l, is not a free S-H band but the remaining S-H---x band of the self-associated benzenethiol. The spectra obtained with the stronger base triethylamine are quite similar (Figs. 8 and 9). At the fundamentals the bands are again very broad and their maxima are, as expected, at lower frequencies than in the case of the pyridine complexes. As triethylamine has relatively strong bands in this part of the spectrum we had to use dilute solutions of propane-1-thiol and triethylamine in CC1,F. The S-H---N band at room temperature is not well defined at these concentrations (it is located at 2420 cm-' in a 5.72 M solution of propane-1-thiol in triethylamine, at 20 "C). However, it can be readily seen at lower temperatures. Its maximum is at 2360 cm-', at "C, and it is clearly asymmetrical, indicating that at lower temperatures, as in the case of pyridine complexes, some more associated complex is also present. On the high frequency side of the 2360 cm-' band, which corresponds to the S-H---S region, some increase of intensity is observed also. Since this spectrum is obtained by subtraction, this is somewhat doubtful (a strong band of triethylamine exists in this region). However, if this

5 BlCCA DE ALENCASTRO AND SANDORFY: ASSOCIATION OF THIOLS Can. J. Chem. Downloaded from by on 12/30/17 FIG. 7. The infrared spectrum ( cm-') of (a) 5.55 M; (b) 2.77 M; and (c) 0.99 M solutions of benzenethiol (-) in CCI, and (-.-) in pyridine, at 20 "C with the absorption due to pyridine subtracted. Vertical axis: 111 log Io/l in cm-' units. FIG. 8. The infrared spectrum ( cm-l) of (-), a 0.94 M solution of propane-1-thiol in CCI3F, and (-.-), a mixt~~re of 0.94 M propane-1-thiol and 0.91 M triethylamine, in CC13F. (a) 20 "C; (b) - 73 "C; (c) "C. (---) region of con~paratively strong bands of triethylamine. The absorption due to triethylamine is subtracted. Vertical axis: 111 log lo/[ in cnl-' units. band really exists it would confirm the presence of a higher complex of the S-H---S-H---N type at lower temperatures. At the overtone (Fig. 9) the maximum is near 2480 cm-' at -98 "C. This is probably due to the S-H---N type association of the 1: 1 complex. Some S-H---S absorption remains and again we cannot say whether it is due to the remaining self-associated S-H---S bond, to some more associated S-H---N species, or to both. Conclusions The main associated species in solutions containing propane-i-thiol or benzenethiol as FIG. 9. The infrared spectrum ( cm-') of a 3.23 M solution of propane-1-thiol (-) in CCI3F and (-.-) in triethylamine. (a) 20 "C; (b)-98 "C. The absorption due to triethylamine is subtracted. Vertical axis: 111 log loll in cm-' units. proton donors, and pyridine or triethylamine as proton acceptors, is a 1 :I complex with a hydrogen bond of the S-H---N type. The related band in the spectrum appears at distinctly lower frequencies than the S-H---S bands. At low temperatures we find evidence for the formation of a more highly associated species of the S-H---S-N type. The overtone of the 1 :I S-H---N complex has been identified. Free S-H bands persist in these solutions at donor-acceptor ratios lower than 1 :3. S-H---K type hydrogen bonds of the self-associated thiol are found for benzenethiol-pyridine mixtures even in the presence of a large excess of pyridipe. We would like to express our thanks to the National Research Council of Canada for financial help. One of us (RBA) would like also to express his gratitude to the National Research Council of Canada and the Conselho Nacional de Pesquisas, Rio de Janeiro, Brazil, for financial assistance under the Brazil-Canada Program for Scientific

6 990 CAN. J. CHEM. VOL. 51, 1973 Exchange, and to the Instituto de Quimica da Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, for a special leave of absence. 1. R. BICCA DE ALENCASTRO and C. SANDORFY. Can. J. Chem. 50, 3594 (1972). 2. W. GORDY and S. C. STANFORD. J. Am. Chem. Soc. 62, 497 (1940). 3. M. 0. BULANIN, G. S. DENISOV, and R. A. PUSHKINA. Opt. and Spectrosc. 6 (6), 491 (1959). 4. R. MATHUR, E. D. BECKER, R. B. BRADLEY, and N. C. LI. J. Phys. Chem. 67, 2190 (1963). 5. S. SINGH, A. S. N. MURTHY, and C. N. R. RAO. Trans. Faraday Soc. 62, 1056 (1966). 6. M. ASSELIN and C. SANDORFY. J. Mol. Struct. 8, 145 (1971). 7. L. J. BELLAMY. The infrared spectra of complex molecules. 2nd ed. Methuen and Co., Ltd. London p. 259.

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