File:Naphthalene resonance.PNG

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English: Naphthalene is an organic compound with formula C

10H 8. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is best known as the main ingredient of traditional mothballs.

Unlike benzene, the carbon–carbon bonds in naphthalene are not of the same length. The bonds C1–C2, C3–C4, C5–C6 and C7–C8 are about 1.36 Å (136 pm) in length, whereas the other carbon–carbon bonds are about 1.42 Å (142 pm) long. This difference, which was established by X-ray diffraction, is consistent with the valence bond model of bonding in naphthalene that involves three resonance structures (as shown); whereas the bonds C1–C2, C3–C4, C5–C6 and C7–C8 are double in two of the three structures, the others are double in only one.
Latviešu: Naftalīna rezonanses struktūras.
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Date/TimeThumbnailDimensionsUserComment
current11:34, 21 January 2014Thumbnail for version as of 11:34, 21 January 20142,490 × 336 (60 KB)DMacks (talk | contribs)redraw from scratch at high-res to current MOS
10:04, 30 May 2007Thumbnail for version as of 10:04, 30 May 2007480 × 80 (3 KB)Yyy (talk | contribs){{GFDL-user-w|en|en wikipedia|Sesqui}} en:The three resonance structures of naphthalene. lv:Naftalīna rezonanses struktūras. Category:Polycyclic aromatic hydrocarbons

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