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  1. A.C. Hardy, J. Opt. Soc. Am. 25, 305 (1935).
  2. G. R. Harrison, Proceedings of the Sixth Spectroscopy Conference (John Wiley, New York, 1939); G. R. Harrison and E. P. Bentley, J. Opt. Soc. Am. 30, 290 (1940).
  3. K. Weber, Zeits. f. physik. Chemie B15, 18 (1931).
  4. E. Rabinowitch, J. Chem. Phys. 8, 551 (1940).
  5. E. Rabinowitch, J. Chem. Phys. 8, 560 (1940).
  6. W. M. Clark, H. D. Gibbs and B. Cohen, Public Health Reports, 40, 1131 (1935).
  7. Earlier papers on thionine and its spectrum are: (a) J. H. Stebbins, Jr., J. Am. Chem. Soc. 6, 304 (1884); (b) A. Bernthsen, Ann. 230, 111, 209 (1885); (c) M. Althausse, and G. Kruss, Ber. 22, 2066 (1889); (d) Formanék and E. Grandmougin, Untersuchung und Nachweis organischer Farbstoffe auf spektroskopischem Wege (Berlin, 1908), Part 1, pp. 143, 150; (Berlin, 1911), Part 2, p. 124. (e) F. Eckert and R. Pummerer, Zeits. f. physik. Chemie 87, 613 (1914); (f) F. Eckert, R. Pummerer and S. Gassner, Ber. 47, 1495 (1914); (g) F. Kehrman, E. Havas and E. Grandmougin, Ber. 46, 2131 (1913); 47, 1881 (1914); (h) F. Kehrman, Ber. 49, 1018 (1916); (i) F. Kehrman and P. Zybs, Ber. 52, 130 (1919); (j) L. Michaelis, M. P. Schubert and S. Granick, J. Am. Chem. Soc. 62, 204, 1802 (1940).
  8. The possibility of an orthoquinoid structure, with the heterocyclic sulfur forming a sulfonium base (as was hypothesized in the older literature7.) cannot be entirely dismissed, although the evidence seems to be against it.7(i).
  9. L. Michaelis and M. P. Schubert, Chem. Rev. 22, 437 (1938).
  10. L. Pauling and co-workers, J. Chem. Phys. 1, 362, 606, 679 (1933); cf. also The Nature of the Chemical Bond, 2nd edition (Cornell University Press, Ithaca, New York, 1940).
  11. C. R. Bury, J. Am. Chem. Soc. 57, 2115 (1935); A. L. Sklar, J. Chem. Phys. 5, 669 (1937); L. Pauling, in H. Gilman, Organic Chemistry (John Wiley, 1938), II, p. 1888; L. Pauling, Proc. Nat. Acad. Sci. 25, 577 (1939); G. N. Lewis and M. Calvin, Chem. Rev. 25, 273 (1939); R. S. Mulliken, J. Chem. Phys. 7, 14, 20, 121, 339, 353, 356, 364, 570 (1939).
  12. (a) W. C. Holmes, Ind. Eng. Chem. 16, 35 (1924), Am. Dyestuff Rep. 16, 429 (1927), J. Am. Chem. Soc. 50, 1923 (1928); (b) G. Körtum, Zeits. f. physik. Chemie B30, 317 (1935), 31, 137 (1935), 31, 1, 243 (1936), 34, 255 (1936); (c) W. E. Speas, Phys. Rev. 31, 539 (1928); (d) G. Scheibe, Kolloid, Zeits. 82, 1 (1938); G. Scheibe and L. Kandler, Naturwiss. 26, 412 (1938); G. Scheibe, A. Schöntag, J. Kopske and K. Meule, Zeits. f. wiss. Phot. 38, 1 (1939); G. Scheibe, A. Schöntag and E. Katheder, Naturwiss. 27, 499 (1939); (e) V. L. Lewshin, Acta Physicochimica, U. R. S. S. 1, 685 (1935), 4, 221 (1936).
  13. Made by Mr. Henry Wayringer, to whom we wish to express our thanks.
  14. E. Rabinowitch and L. F. Epstein, "The polymerization of dye-stuffs in solution. Thionine and methylene blue." Presented at the Symposium on Structure of Molecules and Aggregates of Molecules, Division of Physical and Inorganic Chemistry, American Chemical Society, Columbia University, New York, New York, December 30, 1940 to January 1, 1941. J. Am. Chem. Soc., paper in press.
  15. A. Thiel, A. Dassler and F. Wülfken, Fortschritte Chemie, Physik, u. physik. Chemie 18, 4.3 (1924); E. B. R. Prideaux, Chem. Industry, 45, 664, 678 (1936); cf. W. M. Clark, Determination of Hydrogen Ions (Baltimore, 1928), p. 206.
  16. Cf. reference 14, Fig. 3.
  17. E. Q. Adams and L. Rosenstein, J. Am. Chem. Soc. 36, 1452 (1914).
  18. Adams and Rosenstein (cf. reference 17) also observed irreversible bleaching in acid solution of crystal violet, and studied the kinetics of the bleaching process. In this case the bleaching in acid solutions seemed to be independent of the anion.
  19. Beilstein reports that alkaline solutions of thionine are slowly transformed into [STRUCTURE of Thionolin] [STRUCTURE of Thionol] Both of these reaction products are, however, strongly colored.
  20. We are indebted to Professor L. J. Gillespie and Dr. S. D. Stookey of this laboratory for the special Pd used in these experiments.

Adams, E. Q.

E. Q. Adams and L. Rosenstein, J. Am. Chem. Soc. 36, 1452 (1914).

Bury, C. R.

C. R. Bury, J. Am. Chem. Soc. 57, 2115 (1935); A. L. Sklar, J. Chem. Phys. 5, 669 (1937); L. Pauling, in H. Gilman, Organic Chemistry (John Wiley, 1938), II, p. 1888; L. Pauling, Proc. Nat. Acad. Sci. 25, 577 (1939); G. N. Lewis and M. Calvin, Chem. Rev. 25, 273 (1939); R. S. Mulliken, J. Chem. Phys. 7, 14, 20, 121, 339, 353, 356, 364, 570 (1939).

Clark, W. M.

W. M. Clark, H. D. Gibbs and B. Cohen, Public Health Reports, 40, 1131 (1935).

Cohen, B.

W. M. Clark, H. D. Gibbs and B. Cohen, Public Health Reports, 40, 1131 (1935).

Dassler, A.

A. Thiel, A. Dassler and F. Wülfken, Fortschritte Chemie, Physik, u. physik. Chemie 18, 4.3 (1924); E. B. R. Prideaux, Chem. Industry, 45, 664, 678 (1936); cf. W. M. Clark, Determination of Hydrogen Ions (Baltimore, 1928), p. 206.

Epstein, L. F.

E. Rabinowitch and L. F. Epstein, "The polymerization of dye-stuffs in solution. Thionine and methylene blue." Presented at the Symposium on Structure of Molecules and Aggregates of Molecules, Division of Physical and Inorganic Chemistry, American Chemical Society, Columbia University, New York, New York, December 30, 1940 to January 1, 1941. J. Am. Chem. Soc., paper in press.

Gibbs, H. D.

W. M. Clark, H. D. Gibbs and B. Cohen, Public Health Reports, 40, 1131 (1935).

Hardy, A.C.

A.C. Hardy, J. Opt. Soc. Am. 25, 305 (1935).

Harrison, G. R.

G. R. Harrison, Proceedings of the Sixth Spectroscopy Conference (John Wiley, New York, 1939); G. R. Harrison and E. P. Bentley, J. Opt. Soc. Am. 30, 290 (1940).

Holmes, W. C.

(a) W. C. Holmes, Ind. Eng. Chem. 16, 35 (1924), Am. Dyestuff Rep. 16, 429 (1927), J. Am. Chem. Soc. 50, 1923 (1928); (b) G. Körtum, Zeits. f. physik. Chemie B30, 317 (1935), 31, 137 (1935), 31, 1, 243 (1936), 34, 255 (1936); (c) W. E. Speas, Phys. Rev. 31, 539 (1928); (d) G. Scheibe, Kolloid, Zeits. 82, 1 (1938); G. Scheibe and L. Kandler, Naturwiss. 26, 412 (1938); G. Scheibe, A. Schöntag, J. Kopske and K. Meule, Zeits. f. wiss. Phot. 38, 1 (1939); G. Scheibe, A. Schöntag and E. Katheder, Naturwiss. 27, 499 (1939); (e) V. L. Lewshin, Acta Physicochimica, U. R. S. S. 1, 685 (1935), 4, 221 (1936).

Michaelis, L.

L. Michaelis and M. P. Schubert, Chem. Rev. 22, 437 (1938).

Pauling, L.

L. Pauling and co-workers, J. Chem. Phys. 1, 362, 606, 679 (1933); cf. also The Nature of the Chemical Bond, 2nd edition (Cornell University Press, Ithaca, New York, 1940).

Rabinowitch, E.

E. Rabinowitch and L. F. Epstein, "The polymerization of dye-stuffs in solution. Thionine and methylene blue." Presented at the Symposium on Structure of Molecules and Aggregates of Molecules, Division of Physical and Inorganic Chemistry, American Chemical Society, Columbia University, New York, New York, December 30, 1940 to January 1, 1941. J. Am. Chem. Soc., paper in press.

E. Rabinowitch, J. Chem. Phys. 8, 560 (1940).

E. Rabinowitch, J. Chem. Phys. 8, 551 (1940).

Rosenstein, L.

E. Q. Adams and L. Rosenstein, J. Am. Chem. Soc. 36, 1452 (1914).

Schubert, M. P.

L. Michaelis and M. P. Schubert, Chem. Rev. 22, 437 (1938).

Stebbins, Jr., J. H.

Earlier papers on thionine and its spectrum are: (a) J. H. Stebbins, Jr., J. Am. Chem. Soc. 6, 304 (1884); (b) A. Bernthsen, Ann. 230, 111, 209 (1885); (c) M. Althausse, and G. Kruss, Ber. 22, 2066 (1889); (d) Formanék and E. Grandmougin, Untersuchung und Nachweis organischer Farbstoffe auf spektroskopischem Wege (Berlin, 1908), Part 1, pp. 143, 150; (Berlin, 1911), Part 2, p. 124. (e) F. Eckert and R. Pummerer, Zeits. f. physik. Chemie 87, 613 (1914); (f) F. Eckert, R. Pummerer and S. Gassner, Ber. 47, 1495 (1914); (g) F. Kehrman, E. Havas and E. Grandmougin, Ber. 46, 2131 (1913); 47, 1881 (1914); (h) F. Kehrman, Ber. 49, 1018 (1916); (i) F. Kehrman and P. Zybs, Ber. 52, 130 (1919); (j) L. Michaelis, M. P. Schubert and S. Granick, J. Am. Chem. Soc. 62, 204, 1802 (1940).

Thiel, A.

A. Thiel, A. Dassler and F. Wülfken, Fortschritte Chemie, Physik, u. physik. Chemie 18, 4.3 (1924); E. B. R. Prideaux, Chem. Industry, 45, 664, 678 (1936); cf. W. M. Clark, Determination of Hydrogen Ions (Baltimore, 1928), p. 206.

Weber, K.

K. Weber, Zeits. f. physik. Chemie B15, 18 (1931).

Wülfken, F.

A. Thiel, A. Dassler and F. Wülfken, Fortschritte Chemie, Physik, u. physik. Chemie 18, 4.3 (1924); E. B. R. Prideaux, Chem. Industry, 45, 664, 678 (1936); cf. W. M. Clark, Determination of Hydrogen Ions (Baltimore, 1928), p. 206.

Other (20)

A.C. Hardy, J. Opt. Soc. Am. 25, 305 (1935).

G. R. Harrison, Proceedings of the Sixth Spectroscopy Conference (John Wiley, New York, 1939); G. R. Harrison and E. P. Bentley, J. Opt. Soc. Am. 30, 290 (1940).

K. Weber, Zeits. f. physik. Chemie B15, 18 (1931).

E. Rabinowitch, J. Chem. Phys. 8, 551 (1940).

E. Rabinowitch, J. Chem. Phys. 8, 560 (1940).

W. M. Clark, H. D. Gibbs and B. Cohen, Public Health Reports, 40, 1131 (1935).

Earlier papers on thionine and its spectrum are: (a) J. H. Stebbins, Jr., J. Am. Chem. Soc. 6, 304 (1884); (b) A. Bernthsen, Ann. 230, 111, 209 (1885); (c) M. Althausse, and G. Kruss, Ber. 22, 2066 (1889); (d) Formanék and E. Grandmougin, Untersuchung und Nachweis organischer Farbstoffe auf spektroskopischem Wege (Berlin, 1908), Part 1, pp. 143, 150; (Berlin, 1911), Part 2, p. 124. (e) F. Eckert and R. Pummerer, Zeits. f. physik. Chemie 87, 613 (1914); (f) F. Eckert, R. Pummerer and S. Gassner, Ber. 47, 1495 (1914); (g) F. Kehrman, E. Havas and E. Grandmougin, Ber. 46, 2131 (1913); 47, 1881 (1914); (h) F. Kehrman, Ber. 49, 1018 (1916); (i) F. Kehrman and P. Zybs, Ber. 52, 130 (1919); (j) L. Michaelis, M. P. Schubert and S. Granick, J. Am. Chem. Soc. 62, 204, 1802 (1940).

The possibility of an orthoquinoid structure, with the heterocyclic sulfur forming a sulfonium base (as was hypothesized in the older literature7.) cannot be entirely dismissed, although the evidence seems to be against it.7(i).

L. Michaelis and M. P. Schubert, Chem. Rev. 22, 437 (1938).

L. Pauling and co-workers, J. Chem. Phys. 1, 362, 606, 679 (1933); cf. also The Nature of the Chemical Bond, 2nd edition (Cornell University Press, Ithaca, New York, 1940).

C. R. Bury, J. Am. Chem. Soc. 57, 2115 (1935); A. L. Sklar, J. Chem. Phys. 5, 669 (1937); L. Pauling, in H. Gilman, Organic Chemistry (John Wiley, 1938), II, p. 1888; L. Pauling, Proc. Nat. Acad. Sci. 25, 577 (1939); G. N. Lewis and M. Calvin, Chem. Rev. 25, 273 (1939); R. S. Mulliken, J. Chem. Phys. 7, 14, 20, 121, 339, 353, 356, 364, 570 (1939).

(a) W. C. Holmes, Ind. Eng. Chem. 16, 35 (1924), Am. Dyestuff Rep. 16, 429 (1927), J. Am. Chem. Soc. 50, 1923 (1928); (b) G. Körtum, Zeits. f. physik. Chemie B30, 317 (1935), 31, 137 (1935), 31, 1, 243 (1936), 34, 255 (1936); (c) W. E. Speas, Phys. Rev. 31, 539 (1928); (d) G. Scheibe, Kolloid, Zeits. 82, 1 (1938); G. Scheibe and L. Kandler, Naturwiss. 26, 412 (1938); G. Scheibe, A. Schöntag, J. Kopske and K. Meule, Zeits. f. wiss. Phot. 38, 1 (1939); G. Scheibe, A. Schöntag and E. Katheder, Naturwiss. 27, 499 (1939); (e) V. L. Lewshin, Acta Physicochimica, U. R. S. S. 1, 685 (1935), 4, 221 (1936).

Made by Mr. Henry Wayringer, to whom we wish to express our thanks.

E. Rabinowitch and L. F. Epstein, "The polymerization of dye-stuffs in solution. Thionine and methylene blue." Presented at the Symposium on Structure of Molecules and Aggregates of Molecules, Division of Physical and Inorganic Chemistry, American Chemical Society, Columbia University, New York, New York, December 30, 1940 to January 1, 1941. J. Am. Chem. Soc., paper in press.

A. Thiel, A. Dassler and F. Wülfken, Fortschritte Chemie, Physik, u. physik. Chemie 18, 4.3 (1924); E. B. R. Prideaux, Chem. Industry, 45, 664, 678 (1936); cf. W. M. Clark, Determination of Hydrogen Ions (Baltimore, 1928), p. 206.

Cf. reference 14, Fig. 3.

E. Q. Adams and L. Rosenstein, J. Am. Chem. Soc. 36, 1452 (1914).

Adams and Rosenstein (cf. reference 17) also observed irreversible bleaching in acid solution of crystal violet, and studied the kinetics of the bleaching process. In this case the bleaching in acid solutions seemed to be independent of the anion.

Beilstein reports that alkaline solutions of thionine are slowly transformed into [STRUCTURE of Thionolin] [STRUCTURE of Thionol] Both of these reaction products are, however, strongly colored.

We are indebted to Professor L. J. Gillespie and Dr. S. D. Stookey of this laboratory for the special Pd used in these experiments.

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