Part 10

III. 0.1357 gram gave 0.0807 gram BaSO₄.

C[NH.C₆H₅]₂ / \ / O / / Cal. for C₆H₃——SO₂ \ NO₂ Found. I. II. III.

N = 10.58 10.85 —— —— S = 8.06 —— 8.00 8.16

By this series of transformations it is possible to pass from one anilid to the other, the steps being:

CO.NH.C₆H₅ C=N.C₆H₅ C[NH.C₆H₅]₂ / / \ / \ / / N.C₆H₅ / O / / / / / C₆H₃——SO₂NH.C₆H₅ ➡ C₆H₃——SO₂ ➡ C₆H₃——SO₂ \ \ \ NO₂ NO₂ NO₂

This is of special interest as affording a means of passing from a derivative of one of the chlorides, to a substance derived from the other, by steps that can be clearly followed.

Conclusions.

In the course of this investigation several facts have been established.

1. By the methods described, the symmetrical chloride of paranitroorthosulphobenzoic acid can be obtained in fine crystalline form, perfectly free from its isomer, with an average yield of forty percent.

2. By treatment of the chloride with benzene and aluminium chloride, only one chlorine atom can be replaced by a phenyl group.

3. The barium salt of paranitroorthobenzoyl benzenesulphonic acid, when perfectly pure, crystallizes constantly with seven molecules of water of crystallization.

4. With alcohols, the symmetrical chloride yields directly the acid etherial salt of paranitroorthosulphobenzoic acid, no evidence having been obtained of an intermediate chloro-etherial salt. The unsymmetrical chloride on the other hand yields the intermediate product.

5. With phenols, two series of derivatives are obtained.

(1) With monohydroxy phenols, both etherial salts and sulphonphthaleïns are formed, the former predominating.

(2) With polyhydroxy phenols no etherial salts were obtained, but compounds of the unsymmetrical type, usually containing more than two phenol residues.

6. With aniline an anil and an anilid of symmetrical constitution are formed.

7. With phosphorus oxychloride, the anilid, by loss of water, forms a dianil.

8. This dianil undergoes transformation with

(1) Glacial acetic acid, forming an anilid of unsymmetrical constitution.

(2) Hydrochloric acid forming the anil.

(3) Alcoholic potash, with the formation of colored decomposition products.

Biographical.

The author of the foregoing dissertation was born at Wilkinsburg, Pa., Jan. 29., 1870. Owing to prolonged sickness in childhood his education, prior to entering college, was much interrupted, and was largely confined to instruction received at home.

In the fall of 1887 he entered Wooster University (Ohio), from which institution he received the degree of Bachelor of Arts in 1891. The two following years were spent as a teacher of Sciences in the College of Emporia (Kansas). In 1893 he entered the Johns Hopkins University where he has since been a student of chemistry, with physics and mathematics as subordinate studies.

In 1895 he was appointed University Scholar in Chemistry. During 1895-6 he served as lecture assistant to Prof. Remsen and Dr. Renouf in the undergraduate courses. In the spring of 1896 he was appointed Fellow for the present year.