Page 175 - Arrow Pushing in Inorganic Chemistry A Logical Approach to the Chemistry of the Main Group Elements

FURTHER READING 155
5A.12 SUMMARY

1. In many ways, nitrogen may be viewed as a paradigm of the lighter p-block elements.
It is justly famous for its diverse oxidation states, which include every integral value
between –3 (e.g., NH ) and +5 (e.g., HNO ). It forms stable single, double, and
3 3
triple bonds with other period-2 p-block elements. Nitrogen-based nucleophiles and
electrophiles are ubiquitous in both organic and inorganic chemistry.
2. Amines, both aliphatic and aromatic, are widely employed as nucleophiles and as
–
mild bases. Amide anions (NR ) are used as strong bases in organic chemistry.
2
+
3. Common nitrogen-based electrophiles include the nitrosonium (NO ) and nitronium
+
(NO ) ions, as well as nitrogen halides.
2
4. Elimination of dinitrogen (N ) is a powerful driving force in chemical reactions. A
2
number of important organic transformations hinge around the elimination of N .
2
5. Nitrenes, which are monovalent nitrogen species, are unstable but are useful reactive
intermediates in organic chemistry. We’ll encounter them again in Sections 7.11 and
7.15 in the form of iodine- and bromine-based nitrene transfer agents.
6. The two radical species NO and NO are of great practical importance. Nitrogen
2
dioxide (NO ) is a major pollutant, contributing to acid rain as well as to respiratory
2
illnesses. Nitric oxide (NO) is a ubiquitous signaling molecule in biology.
FURTHER READING

Besides the texts listed in Appendices 1 and 2, the following books cover some of the special topics
discussed in this chapter.

1. Stoltzenberg, D. Fritz Haber: Chemist, Nobel Laureate, German, Jew: A Biography; Chemical
Heritage Foundation, 2005; 336 pp. An excellent biography.
2. Bailey, P. D.; Morgan, K. M. Organonitrogen Chemistry; Oxford University Press: Oxford, 1996;
96 pp.
3. Favery, D. E.; Gudmundsdottir, A. D., eds. Nitrenes and Nitrenium Ions; John Wiley & Sons, Inc.:
Hoboken, NJ, 2013; 586 pp. A major, up-to-date survey of an important field.
4. Gilchrist, C. L.; Rees, C. W. Carbenes, Nitrenes and Arynes; Nelson: London, 1969; 131 pp. A
short classic.
5. Butler, A. R.; Nicholson, R. Life, Death and Nitric Oxide; Royal Soc.: Cambridge, 2003; 140 pp.
A readable account of the biological role of NO.
6. Ignarro, L. J., ed. Nitric Oxide: Biology and Pathobiology, 2nd ed. Academic: Waltham, MA,
2009; 845 pp. A definitive volume with contributions by leading researchers.