The cross-conjugated macrocycles 8a-e and acyclic model compound 12 have been synthesized and thoroughly analyzed by 1 H and 13 C NMR, UV, IR, and Raman spectroscopies, and by X-ray crystallography. The increasing ring strain and resultant changes in the double and triple bond orders are clearly detailed in the Raman and 13 C NMR spectra, as well as in the X-ray structures. Correlations between 13 C NMR shifts, bond angles, and Raman frequencies are essentially linear for the butadiynyl and olefinic moieties. The most highly strained system, 8a, displays interior alkylidene bond angles that are reduced to 108°and alkyne angles reduced to as little as 155°. The electronic absorption spectrum of 8a shows evidence of through-space homoconjugation that is manifested as a bathochromic shift of the absorption band arising from the in-plane π-system. The absorption bands from the out-of-plane π-electron systems of the more strained cycles 8a and 8b show slight bathochromic shifts as compared with the less strained systems 8c-e and acyclic 12. Ring strain, however, has a surprisingly small effect on the electronic absorption energies of these macrocycles.