What do the following different kind of bonds mean?

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Although this answer to the question "What are the meanings of dotted and wavy lines in structural formulas?" does describes some of the bonds, it does not provide a complete description and some bonds are not mentioned. Also, the question has a dotted-line bond, which maybe misleading.

  • 1
    $\begingroup$ While your effort in aggregating info about graphical representations of chemical bonds is appreciated, but I don't think posting a different question with a subset (which is also far from complete) of notations from What are the meanings of dotted and wavy lines in structural formulas? is justified. Posting textual description as an image pretty much nullifies the distinction as this question won't be discovered on its own. Maybe the previous question's answer should be a wiki. Also, IMO an MD table would be more clear and searchable. $\endgroup$
    – andselisk
    Jun 11 at 9:40
  • $\begingroup$ @andselisk the previous answer did not cover all the different plain/stereobonds, which is why i decided on posting this. Thank you for the suggestion, I have formatted the description of bonds as a table. $\endgroup$
    – ananta
    Jun 11 at 10:04
  • $\begingroup$ @NilayGhosh hope the latest edit addresses your comment. $\endgroup$
    – ananta
    Jun 11 at 10:24
  • $\begingroup$ Then make a new answer in that post addressing other type of bonds initially not mentioned. I also agree with andselisk's suggestion. $\endgroup$ Jun 11 at 10:26
  • $\begingroup$ @NilayGhosh an accurate description of most commonly used bonds may be helpful to the community. I have incorporated andselisk's suggestions. As I mentioned, the other question is misleading. This question is more thorough, and the answer more accurate. I am not claiming to describe the entirety of stereochemistry in a single page, there is a reason several books have been written on it; and as mentioned, this is a topic of ongoing discussion and developments. $\endgroup$
    – ananta
    Jun 11 at 10:31

1 Answer 1


Disclaimer: This is topic of ongoing discussion, and different authors use different conventions. This answer is, mostly, based on IUPAC recommendations (2006). This is not a complete list, as there are a vast number of representations for stereochemistry of a compound, Fischer and Newmann projections to name two. Furthermore, in biochemistry, the representations are different.

This page covers the topic in more detail with lots of examples.

Name Representation Meaning
Dashed bond dashed bond representation Partial bond in plain of paper or of unspecified stereochemistry. Also represents hydrogen bonds. Also represents bonds with known relative and unknown absolute configuration in an enantiopuric product; similar to hashed wedged bond.
Solid bond solid bond representaion Bond in plain of paper or unspecified stereochemistry.
Hashed wedged bond Hashed wedged bond representation Narrow end: towards reader; wide end: away from reader.
Hashed unwedged bond Hashed unwedged bond representation Both atoms are below the plain of the paper. Also represents configuration of racemates.
Solid wedged bond Solid wedged bond representation Narrow end: away from reader; wide end: towards reader.
Solid unwedged bond Solid unwedged bond representation Both atoms are above the plain of the paper. Also represents configuration of racemates.
Hollow unwedged bond enter image description here Bonds with known relative and unknown absolute configuration in an enantiopuric product; similar to solid wedged bond
Wavy bond Wavy bond representation Bond with unknown stereochemsitry. Also represents an unknown moiety.
Arrow bond Arrow bond representation Dative bond in plain of paper or with unknown stereochemsitry.

Controversy Surrounding Hashed Wedged Bond

There is a bit of controversy surrounding the hashed bond.$^\text{1}$

Unfortunately, bonds below the plane of the drawing have historically been represented in many different ways. Each of those representations has involved a bond drawn with small line segments either coincident with or perpendicular to the main axis of the bond. The two schools of thought that prefer the use of a hashed wedge bond assign it two directly opposite interpretations—one school says that the atom at the narrow end should be considered in the plane of the paper, while the other says that the atom at the wide end should be so considered. Additionally, a dashed line often represents a partial bond, delocalization, or a hydrogen bond. The biggest problem is that there is no way to intuit an author’s desired meaning from a chemical structure drawing alone.

Hashed and Solid Wedged Bonds

In the article,$^\text{1}$ IUPAC recommends using the hashed wedge bond in a similar way to that of the solid wedged bond:

In cases where such below-the-plane bonds are required, there is no option that will please everyone. Earlier recommendations 12 proposed the use of an unwedged hashed bond, but today such bonds are in fact encountered in the literature least frequently of all options. This document now recommends the use of a hashed wedged bond interpreted in a sense similar to the solid wedged bond (starting from an atom in the plane of the drawing at the narrow end of the wedge). This recommendation is made primarily because the hashed wedge is easier to analyze visually than the unwedged type, particularly when it is used in a sense similar to the wedged bold bond.

The unwedged hashed or solid bonds are used specifically to indicate that both atoms are below or above the plane, respectively:$^\text{1}$

Strictly speaking, unwedged bold and hashed lines show that both atoms are above or below the plane of the drawing (as is used in Haworth drawings of carbohydrates).

Hashed and Solid Unwedged Bonds

The hollow wedged bond represents bonds with known relative but unknown absolute configuration in enantiopuric compounds. And unwedged hashed and solid bonds are also represents recemates:$^\text{2}$

bonds according to enantiostatus of compound

Wiggly Lines

Although it is not recommended by IUPAC, some authors (e.g., Clayden J., Greeves N., and Warren S. who call it wiggly lines) do use the wavy bond to show an unknown moiety: $^\text{3}$

wiggly line representation in chemistry

The Dotted-Line Bond

Note: a dotted-line bond has not been recommended by IUPAC. I have seen it represent an ionic interaction, such as between carboxylate and sodium ions.


  1. Brecher, J. (2006). Graphical Representation Of Stereochemical Configuration. Pure Appl. Chem., 78(10), 1897–1970. 10.1351/pac200678101897
  2. Maehr, H. (2002). Graphic Representation of configuration in Two-Dimensional Space. Current Conventions, Clarifications, and Proposed Extensions. J. Chem. Inf. Comput. Sci, 42, 894-902. 10.1021/ci025518w
  3. Clayden J., Greeves N., and Warren S. (2012). Organic Chemistry, $\textit{2}^\textit{nd}$ ed. Oxford University Press Inc., New York
  • 3
    $\begingroup$ Sorry, bit this is not a "complete list of plain bonds", and what is depicted in your answer as a plain bond, is not one. Aromatic, single up/down, single or double, single or aromatic, double or aromatic, double cis / trans etc., not to mention more obscure bond notations from biochem are missing. $\endgroup$
    – andselisk
    Jun 11 at 9:45
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    $\begingroup$ @andselisk thank you for your suggestion, which has been added to the disclaimer. What you are referring to has not been mentioned in IUPAC recommendation 2006, also I am not talking about stereodescriptors, which are different from plain/stereobonds. $\endgroup$
    – ananta
    Jun 11 at 10:17

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