N-(ortho-alkylphenyl)carbazoles (1) have proven to be good systems to study when comparing them to 9-(ortho-alkylphenyl)fluorenyl anions (2). We have demonstrated through X-Ray crystallographic studies on carbazole systems, and Gaussian calculations on both carbazole and 9-fluorenyl anion systems, that both carbazoles and 9-fluorenyl anions are not only isoelectronic, but geometrically similar. Because of their similarities, the carbazole system makes a convenient air-stable species to study the structure of the 9-fluorenyl anion. We have demonstrated through asymmetric N-(ortho-alkylphenyl)carbazoles that the rotation about the nitrogen-phenyl bond is restricted, and may not rotate at all. We can also say that the same probably holds true for their isoelectronic fluorenyl anions. A series of compounds have been synthesized and will be discussed.