Double bonds traditionally appear in three orientations relative to the imaginary line connecting the centers of the atoms on either end of the bond. The double bond may be offset on either side of the center, or it may straddle the center exactly.
If the double bond is offset, one segment should be centered exactly, while the other one is offset. The segment of the double bond that is offset should usually be shortened at both ends. The amount of the shortening will depend on the spacing between the two segments and on the angles of the ajoining bonds. For best appearances. The endpoints of the second segment should be positioned so that they fall on the bisector of the angle between the double bond and its adjoining bond. If a bond is unsubstituted on one end, or if the only substitution on that end is trans relative to the second segment, then the segment should not be shortened on that end.
Because the amount of shorting is dependent on the adjacent angles, it is most pronounced in small rings.
In contrast, centered double bonds should be extended to join seamlessly with the nearest substituent on either end.
If a double bond has more substituents on one side than on the other, the double bond should be offset to that side.
| RECOMMENDED | RECOMMENDED | RECOMMENDED | AVOID | AVOID | AVOID | AVOID | AVOID | AVOID |
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In cases where the double bond has three substituents, and the two substituents on the same end of the double bond are identical or nearly so, it is reasonable for a double bond to be drawn in a centered configuration to emphasize the local symmetry. Since a centered double bond with a single substituent on an unlabeled carbon may look odd, this style should only be used when the side of the double bond with one substituent has an atom label.
| RECOMMENDED | RECOMMENDED | AVOID | AVOID |
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Double bonds with two or more substituents on one end and no substituents on the other should be drawn with the two segments of the double bond centered relative to its atoms. Double bonds of this type are necessarily acyclic, and are most commonly found in carbonyl and acid functional groups.
| RECOMMENDED | RECOMMENDED | AVOID | AVOID | AVOID | AVOID |
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Double bonds with one substituent on each end, and with those two substituents trans to each other should be drawn with one segment offset. The directionality of the offset is not prescribed for acyclic bonds, and may be selected by the author according to the needs of the diagram. For trans bonds that are cyclic, the double bond should be offset towards the center of the ring (bonds of this type are uncommon).
| RECOMMENDED | RECOMMENDED | RECOMMENDED | AVOID | AVOID | AVOID |
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Double bonds with two substituents on each end should normally be drawn with one segment offset. If one substituent on either end is a member of a ring, the double bond should be offset toward the center of that ring. If the double bond is a fusion bond between two rings, the bond should be offset in the direction of whichever ring has the greatest number of other double bonds. If both rings have the same number of double bonds, the double bond may be offset in either direction according to the preferences of the author.
| RECOMMENDED | AVOID | AVOID | RECOMMENDED | RECOMMENDED | AVOID |
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| RECOMMENDED | AVOID | AVOID | RECOMMENDED | RECOMMENDED | AVOID |
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Acyclic double bonds may also be offset in either direction according to the needs of the author. It is also acceptable to draw a double bond with four substitutents in a centered configuration, but this style should be restricted to acyclic bonds where both substituents on one end are identical or nearly so.
| RECOMMENDED | RECOMMENDED | RECOMMENDED | RECOMMENDED | RECOMMENDED | AVOID |
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